Aryl-mercapto anthraquinone dyestuffs, their preparation and use and dichroic material containing aryl-mercapto anthraquinone dyestuffs

ABSTRACT

Anthraquinone dyestuffs of the formula ##STR1## in which R 1  represents alkyl, aralkyl, --CO--X-alkyl, --CO-- X-aralkyl, --CO--X-aryl, --O-alkyl, --O-aralkyl, --O-- aryl, --CN, --NO 2 , --CF 3 , halogen or a heterocyclic radical and 
     R 2  represents H or R 1 , 
     X representing O, S, NH or a direct bond and 
     Y 1 , Y 2 , Y 3  and Y 4  denoting hydrogen, --NH 2 , --OH, halogen, --NO 2  or an arylmercapto group and at least one of the substituents Y 1  -Y 4  representing an arylmercapto group, 
     it being also possible for the alkyl, aryl, aralkyl and heterocyclic radicals mentioned for R 1  and Y 1  -Y 4  to be substituted, the preparation and use thereof, and dichroic material containing these anthraquinone dyestuffs.

The invention relates to new anthraquinone dyestuffs of the formula ##STR2## their use in dyeing, and dichroic material, preferably in the form of liquid-crystal phases, containing at least one of these anthraquinone dyestuffs.

In formula (I),

R₁ represents alkyl, aralkyl, --CO--X--alkyl, --CO--X--aralkyl, --CO--X--aryl, --O--alkyl, --O--aralkyl, --O--aryl, CN, NO₂, CF₃, halogen or a heterocyclic radical,

R₂ represents H or R₁,

X representing O, S, NH or a direct bond, and

Y₁, Y₂, Y₃ and Y₄ represent hydrogen, NH₂, OH, Hal, NO₂ or an arylmercapto group, and at least one of the substituents Y₁ to Y₄ denotes the arylmercapto group. The alkyl, aralkyl, aryl and heterocyclic radicals mentioned for R₁ and also Y₁ -Y₄ can be substituted.

In particular, Y₁, Y₂, Y₃ and Y₄ represent the following combinations of four:

                  TABLE 1     ______________________________________     Y.sub.1     Y.sub.2    Y.sub.3    Y.sub.4     ______________________________________     S--Ar       S--Ar      S--Ar      NH.sub.2     S--Ar       S--Ar      NH.sub.2   S--Ar     S--Ar       NH.sub.2   S--Ar      S--Ar     NH.sub.2    S--Ar      S--Ar      S--Ar     S--Ar       S--Ar      S--Ar      H     S--Ar       S--Ar      H          S--Ar     S--Ar       H          S--Ar      S--Ar     H           S--Ar      S--Ar      S--Ar     S--Ar       S--Ar      NH.sub.2   NH.sub.2     NH.sub.2    NH.sub.2   S--Ar      S--Ar     S--Ar       NH.sub.2   NH.sub.2   S--Ar     NH.sub.2    S--Ar      S--Ar      NH.sub.2     S--Ar       NH.sub.2   S--Ar      NH.sub.2     NH.sub.2    S--Ar      NH.sub.2   S--Ar     S--Ar       S--Ar      NH.sub.2   OH     S--Ar       S--Ar      OH         NH.sub.2     NH.sub.2    OH         S--Ar      S--Ar     OH          NH.sub.2   S--Ar      S--Ar     S--Ar       NH.sub.2   S--Ar      OH     NH.sub.2    S--Ar      OH         S--Ar     S--Ar       OH         S--Ar      NH.sub.2     OH          S--Ar      NH.sub.2   S--Ar     S--Ar       S--Ar      NH.sub.2   Hal     S--Ar       S--Ar      Hal        NH.sub.2     NH.sub.2    Hal        S--Ar      S--Ar     Hal         NH.sub.2   S--Ar      S--Ar     S--Ar       NH.sub.2   S--Ar      Hal     NH.sub.2    S--Ar      Hal        S--Ar     S--Ar       Hal        S--Ar      NH.sub.2     Hal         S--Ar      NH.sub.2   S--Ar     S--Ar       S--Ar      NH.sub.2   H     S--Ar       S--Ar      H          NH.sub.2     NH.sub.2    H          S--Ar      S--Ar     H           NH.sub.2   S--Ar      S--Ar     S--Ar       NH.sub.2   S--Ar      H     NH.sub.2    S--Ar      H          S--Ar     S--Ar       H          S--Ar      NH.sub.2     H           S--Ar      NH.sub.2   S--Ar     S--Ar       OH         S--Ar      OH     OH          S--Ar      OH         S--Ar     S--Ar       OH         S--Ar      Hal     OH          S--Ar      Hal        S--Ar     S--Ar       Hal        S--Ar      OH     Hal         S--Ar      OH         S--Ar     S--Ar       S--Ar      OH         H     S--Ar       S--Ar      H          OH     OH          H          S--Ar      S--Ar     H           OH         S--Ar      S--Ar     S--Ar       OH         S--Ar      H     OH          S--Ar      H          S--Ar     S--Ar       H          S--Ar      OH     H           S--Ar      OH         S--Ar     S--Ar       Hal        S--Ar      H     Hal         S--Ar      H          S--Ar     S--Ar       H          S--Ar      Hal     H           S-- Ar     Hal        S--Ar     S--Ar       S--Ar      H          H     H           H          S--Ar      S--Ar     S--Ar       H          S--Ar      H     H           S--Ar      H          S--Ar     S--Ar       NH.sub.2   NH.sub.2   NH.sub.2     NH.sub.2    S--Ar      NH.sub.2   NH.sub.2     NH.sub.2    NH.sub.2   S--Ar      NH.sub.2     NH.sub.2    NH.sub.2   NH.sub.2   S--Ar     S--Ar       NH.sub.2   NH.sub.2   OH     NH.sub.2    S--Ar      OH         NH.sub.2     NH.sub.2    OH         S--Ar      NH.sub.2     OH          NH.sub.2   NH.sub.2   S--Ar     S--Ar       OH         NH.sub.2   NH.sub.2     OH          S--Ar      NH.sub.2   NH.sub.2     NH.sub.2    NH.sub.2   S--Ar      OH     NH.sub.2    NH.sub.2   OH         S--Ar     S--Ar       NH.sub.2   OH         NH.sub.2     NH.sub.2    S--Ar      NH.sub.2   OH     OH          NH.sub.2   S--Ar      NH.sub.2     NH.sub.2    OH         NH.sub.2   S--Ar     S--Ar       NH.sub.2   NO.sub.2   NH.sub.2     NH.sub.2    S--Ar      NH.sub.2   NO.sub.2     NO.sub.2    NH.sub.2   S--Ar      NH.sub.2     NH.sub.2    NO.sub.2   NH.sub.2   S--Ar     S--Ar       NH.sub.2   NH.sub.2   H     NH.sub.2    S--Ar      H          NH.sub.2     NH.sub.2    H          S--Ar      NH.sub.2     H           NH.sub.2   NH.sub.2   S--Ar     S--Ar       H          NH.sub.2   NH.sub.2     H           S--Ar      NH.sub.2   NH.sub.2     NH.sub.2    NH.sub.2   S--Ar      H     NH.sub.2    NH.sub.2   H          S--Ar     S--Ar       NH.sub.2   H          NH.sub.2     NH.sub.2    S--Ar      NH.sub.2   H     H           NH.sub.2   S--Ar      NH.sub.2     NH.sub.2    H          NH.sub.2   S--Ar     S--Ar       NH.sub.2   H          H     NH.sub.2    S--Ar      H          H     H           H          S--Ar      NH.sub.2     H           H          NH.sub.2   S--Ar     S--Ar       H          NH.sub.2   H     H           S--Ar      H          NH.sub.2     NH.sub.2    H          S--Ar      H     H           NH.sub.2   H          S--Ar     ______________________________________

In Table 1, Ar denotes aryl and Hal denotes halogen.

Possible substituents for the aryl radicals are, in particular, alkyl, such as C₁ -C₇ --alkyl, cycloalkyl, such as C₃ -C₇ --cycloalkyl, aralkyl, such as C₁ -C₄ --alkylaryl, trifluoromethyl, aryl, halogen, such as fluorine, chlorine or bromine, alkoxy, such as C₁ -C₆ --alkoxy, aryloxy, such as phenoxy and naphthyloxy, or --COOT in which T denotes an organic radical.

Examples of suitable aryl radicals are phenyl, biphenyl, naphthyl, indanyl and tetrahydronaphthyl; phenyl is preferred. Preferred substituents in the aryl radicals are C₁ -C₇ --alkyl, in particular methyl and tert.butyl, halogen, in particular Cl and F, phenyl and --COOT.

Alkyl preferably denotes C₁ -C₇ --alkyl and can optionally be substituted by halogen, such as fluorine or chlorine, C₁ -C₄ --alkoxy, hydroxyl, cycloalkyl, in particular cyclopentyl or cyclohexyl, or the cyano group, and/or can optionally be interrupted in the C chain by one or more O and/or S atoms.

Aralkyl denotes especially a C₁ -C₄ --alkylaryl radical in which the aryl radical can optionally be substituted as described above for aryl.

Heterocyclic radicals are especially optionally substituted and/or fused rings carrying 5-ring or 6-ring heterocyclic structures of the oxazole, oxdiazole, thiazole, thiadiazole, imidazole, triazole, oxazoline or dihydro-H-oxazine series.

T preferably represents a C₁ -C₈ --alkyl radical in which the C chain can be interrupted by O and/or S, and which can be substituted by halogen, hydroxyl, C₁ -C₄ --alkoxy, cycloalkyl, in particular cyclopentyl or cyclohexyl, or optionally substituted aryl, in particular optionally substituted phenyl, or T represents optionally substituted aryl, in particular optionally substituted phenyl.

Compounds of the formula (I) which are particularly important within the scope of the present invention are those in which at least one of the substituents Y₁, Y₂, Y₃ and Y₄ represents NH₂ and/or OH, and, additionally, at least one represents --S--aryl, and the remaining substituents, Y₁, Y₂, Y₃ and Y₄, if any, denote hydrogen.

Dyestuffs of the formula I which are also of particular interest are those in which 1-3 of the substituents Y₁, Y₂, Y₃ and Y₄ represent --NH₂ and/or --OH and, in addition 3-1 of the substituents Y₁, Y₂, Y₃ and Y₄ represent optionally substituted arylmercapto.

Other compounds which are particularly important are those of the formulae ##STR3##

The individual substituents in the formulae II-XIV have the following meanings:

Y₅ denotes --NH₂, --OH or optionally substituted arylmercapto;

Y₂ ', Y₃ ' and Y₄ ' denote optionally substituted arylmercapto;

X₁ denotes --O--, --S-- or ##STR4## R₄ and R₅ denote optionally substituted alkyl which can be interrupted in the C chain by one or more O and/or S atoms, or denotes optionally substituted aryl;

R₃ denotes optionally substituted alkyl which can be interrupted in the C chain by one or more O and/or S atoms, in particular methyl, ##STR5## --OR₄ or --SR₄ ; R₃ ' denotes optionally substituted alkyl which can be interrupted in the C chain by one or more O and/or S atoms, in particular methyl or ##STR6## R₃ " denotes --OR₄ or --SR₄ ; and Y₆ and Y₇ denote --NH₂, --OH or --SR₄, it being necessary for one of the two radicals Y₆ and Y₇ to be --SR₄.

The compounds of the formula (I) are prepared by methods which are in themselves known, such as are described, for example, in Houben-Weyl, Methoden der organischen Chemie ("Methods of Organic Chemistry"), 4th edition, 1979, G. Thieme Verlag, Stuttgart, Volume 7/3c.

The introduction of the arylmercapto radical is effected by reacting an appropriate halogenoanthraquinone or nitroanthraquinone or the corresponding anthraquinonesulphonic acid with an appropriate thiophenol or an organic solvent, for example in an alcohol or in dimethylformamide, dimethyl sulphoxide or N-methylpyrrolidone, or, when reacting an anthraquinonesulphonic acid, also in water, and in the presence of acid-binding agents, such as alkali metal carbonates, hydroxides, oxides or acetates or alkaline earth metal carbonates, hydroxides, oxides or acetates, or in the presence of organic acid-binding agents, such as triethylamine. In this reaction, if the reaction conditions are suitable, nitro groups frequently react preferentially, so that, in the case of some nitrohalogenoanthraquinones, it is possible to carry out the reaction in such a way that only the nitro groups are replaced.

The amino groups are introduced in a known manner, either by reducing a nitro group or by subjecting a corresponding halogenoanthraquinone to tosylamide fusion, followed by scission. In dinitroanthraquinones, such as 1,5-dinitro-4,8-dihydroxyanthraquinone, it is frequently possible to replace or reduce the nitro groups in stages, so that the remaining nitro group is available for further reactions.

In general, the compounds are obtained in a state of purity which is not sufficient for them to be used in liquid-crystal compositions, so that additional purification measures, such as recrystallisation, column chromatography or liquid-liquid partition, are necessary.

The invention also relates to dichroic material, preferably in the form of liquid-crystal phases, containing at least one dyestuff of the formula (I). The liquid-crystal compositions are preferably used in optoelectronic display elements.

The dyestuffs which are used in accordance with the invention possess an excellent fastness to light, a high order parameter and, to a predominant extent, a colour density in liquid-crystal materials which is sufficiently high for industrial use. The properties mentioned are of decisive importance for suitability as dyestuffs in optoelectronic display elements operating on the guest-host principle (German Offenlegungsschrift No. 3,028,593).

Optoelectronic display elements generally consist of two sheets of glass arranged parallel to one another (at a distance of 5-50μ). The liquid-crystal material is embedded between electrodes mounted on the inner sides of the glass sheets. The proper functioning of an optoelectronic display depends on the oriented structure of the liquid crystals, which can be modified by the electric field applied.

The oriented structure of the liquid-crystal materials can communicate itself to suitable dyestuffs, so that the latter participate in the structure as "guests".

The dyestuffs according to the invention are used as a solution of a nematic liquid-crystal mixture in guest-host displays of known construction and mode of operation (Heilmeyer et al, Mol. Crystals and Liquid Cryst. 8, 293-309 (1969) and German Offenlegungsschriften Nos. 2,639,675 and 2,568,568). The liquid-crystal material used as the host phase contains at least one dyestuff of the formula (I), and can also contain further dyestuffs. The latter may or may not possess dichroic properties.

The solution consists of about 0.01 to about 30% by weight, preferably about 0.1 to about 10% by weight, of dyestuff (as the guest) and of the host phase, which consists mainly of nematic, liquid-crystal material, and which can contain further additives, for example additives for achieving a cholesteric orientation.

The invention also relates, therefore, to liquid-crystal materials containing anthraquinone dyestuffs of the formula (I). The liquid-crystal material preferably has positive dielectric anisotropy and can be employed in optoelectronic display devices.

Of the various states of order of liquid-crystal materials, the nematic and cholesteric states are preferred, in accordance with the definitions, such as are stated, for example, in R. Steinstrasser and L. Pohl, Angew. Chem. 85, 706 (1973).

In the zero-field state, it is possible to distinguish two orientations of the liquid-crystal material, which depend on the property of the phase boundary and thus on the pretreatment of the glass sheets. The texture is described as homotropic or homogeneous, depending on whether the long axis of the molecules of which the liquid-crystal phase consists are oriented vertically or horizontally in relation to the surface of the sheet. The techniques for producing suitable surfaces are known (Ullmann, 4th Edition (1976), Volume XI, page 657 et seq). The dielectric anisotropy is dependent on the dipole properties of the liquid-crystal compounds. It is positive when the electric field produces a homotropic alignment and negative when this alignment becomes homogeneous. It is preferable to use this dyestuffs according to the invention in liquid-crystal materials having positive dielectric anisotropy. Examples of suitable liquid-crystal materials are mixtures containing mainly 4-cyanobiphenyls. An example is afforded by mixture E 7 of BDH Chemicals Ltd. (U.K.), or those which contain mainly 1-(4-cyanophenyl)-4-alkylcyclohexanes. An example of these is mixture ZLI 1132 of Merck (Darmstadt). Other suitable mixtures are those of the classes of substances mentioned previously with (4-cyanophenyl)-pyrimidines, for example mixture ROTN 30 of F. Hoffmann-La Roche.

Further examples of commercially available and suitable liquid-crystal mixtures which may be mentioned for positive anisotropy of dielectric constant and products based on cyanopyrimidines and cyanoesters, and also mixtures of BCH, PCH and PCH--esters and PCH, BCH, PCH--esters and terphenyl (for example "ROTN 402", "ROTN 103", "Merck 1221 TNC", "Merck 1291 TNC", "Merck 1691", and "Merck 1840").

Additionally, however, it is possible to employ a large number of other components, suitable mixtures generally being those containing the constituent mentioned. Compounds belonging to the following classes of substances are particularly suitable: ##STR7##

Each of the benzene rings present can be substituted by one or more substituents, for example fluorine. In these formulae

R is an alkyl group, a trans-1,4-substituted cyclohexane ring or a 1,4-substituted bicyclo-[2,2,2]octane ring,

X₂ is a 1,4-phenylene, 4,4'-biphenylene or 2,6-naphthylene group,

Z₁ is CN, R', OR' or CO--O--X₂ --Z₂,

Z₂ is CN, R' or OR' and

G and L are --CH₂ CH₂ --, --CH═CH-- or --C.tbd.C--.

R' has the same meaning as R.

As well as the liquid-crystal compounds and the dyestuff, the liquid-crystal material can contain further customary additives, for example optically active compounds which can convert a nematic phase into a cholesteric phase, or substances for reducing the threshold voltage etc.

The quality of the guest-host interaction can be indicated by the mean deviation of the geometrical axis of the dyestuff molecule from the preferential orientation which is determined by the molecules of the liquid-crystal material. It is possible to define an order parameter S which takes account of the mean deviation and assumes a value of 1.0 in the event of ideal order. In practice, this value is not achieved; the S values are, on the contrary, <1.0. Owing to different techniques of measurement, the values quoted in the literature are not comparable as they stand. The definition of the order parameter and its significance are described by D. L. White and G. N. Taylor, J. Appl. Phys. (5) 1974, 4718-4723, or, for example, in European Laid-Open Application 2,104. The S values of some of the claimed compounds are listed in Tables 2 and 3.

For industrial use, dyestuffs having a high order parameter are particularly valuable. However, they must have a number of other properties. Their photochemical stability must be very good and their colour shade must neither fade nor bleach in the light. In addition, they must have a good stability to chemicals in the liquid-crystal medium, which has a complex composition. Finally, the dyestuff must have a high colour density and must not crystallise even at continuing low temperatures.

It is evident that there are not many substances which fulfill the totality of all the properties in a satisfactory manner. Dichroism of light absorption as a function of the orientation of the host liquid crystals is a necessary requirement for dyestuffs to be usable.

Rendering the dyestuffs adequately soluble while maintaining their dichroic fastness and colour properties presents a particular difficulty. A large number of tests are necessary just for optimising the solubility.

Anthraquinones have already been known in the literature for a fairly long time as dichroic dyestuffs, for example from the following literature references: German Offenlegungsschrift No. 2,363,219, U.S. Pat. No. 3,864,022, U.S. Pat. No. 3,975,285, German Offenlegungsschriften Nos. 2,418,364, 2,815,335, 2,920,730, 3,006,744 and 2,082,196, European Patent No. A1-2,104, European Patent No. A1-49,035 and Japanese Patent Applications Nos. 56/112,967, 56/38,376 and 56/10,583.

All the compounds which are known from the literature prove to be in need of improvement in respect of order parameter, colour density, stability to light and/or colour stimulus specifications.

Depending on their substitution, the dyestuffs according to the invention provide yellow to blue shades of good fastness to light and tinctorial strength.

The dyestuffs which can be employed in accordance with the invention are of particular value for formulating black mixtures for liquid-crystal compositions in combination with anthraquinone and azo dyestuffs. Examples of anthraquinone dyestuffs which are suitable for such combinations are known from European Laid-Open Application No. 26,004, German Offenlegungsschriften Nos. 3,009,940 and 3,009,974, European Laid-Open Application No. 34,832 and German Offenlegungsschriften No. 2,903,095, 3,028,593, 3,036,853 and 3,038,372.

The dyestuffs according to the invention are also particularly suitable for dyeing synthetic polymers, for example fibres or plastics based on polyesters, polyamides, cellulose esters or polycarbonates, by processes which are customary per se.

In the following text, the "Colour Index Hue Indication Chart" (Society of Dyers and Colourists, U.K., and American Association of Textile Chemists and Colorists, U.S.A.) is abbreviated to "CIHIC".

EXAMPLE 1

(a) 95 g of 1-amino-2-methyl-4-bromoanthraquinone and 41 g of anhydrous potassium carbonate are introduced into 500 cc of dimethylformamide, 55 g of 4-tert.-butylthiophenol are added to the mixture, and the latter is heated to 125° to 130° C. in the course of 1 hour and is kept at this temperature until, after approx. 3 hours, the reaction is complete. After cooling to approx. 70° C., the reaction mixture is diluted with 500 cc of methanol and is allowed to cool completely. The dyestuff which has crystallised out is then filtered off with suction, washed with methanol and hot water and dried at 60° C. This gives 66 g (corresponding to 54% of theory) of 1-amino-2-methyl-4-(4-tert.-butylphenylmercapto)-anthraquinone, which is recrystallised from dimethylformamide to remove a blue by-product.

The colour shade of the dyestuff when adsorbed onto silica gel is a bluish-tinged red which has Indicator Number 10 (CIHIC).

(b) 0.5% of the dyestuff prepared in Example 1a is dissolved in a nematic phase, consisting of a mixture of approx. 24% of trans-4-heptyl-(4-cyanophenyl)-cyclohexane, 37% of trans-4-pentyl-(4-cyanophenyl)-cyclohexane, 26% of trans-4-propyl-(4-cyanophenyl)-cyclohexane and 12% of trans-4-pentyl-(4'-cyanobiphenylyl)-cyclohexane. This gives a liquid-crystal mixture which has a bluish-tinged red colour and in which the dyestuff has an order parameter S of 0.69.

(c) 0.5% of the dyestuff prepared in Example 1a is dissolved in a liquid-crystal phase consisting of 51% of 4'-n-pentyl-4-cyanobiphenyl, 25% of 4'-n-heptyl-4-cyanobiphenyl, 16% of 4'-n-octyl-4-cyanobiphenyl and 8% of 4"-n-pentyl-4-cyanoterphenyl. This gives a liquid-crystal mixture which has a bluish-tinged red colour and in which the dyestuff has an order parameter S of 0.70.

Similar good order parameters are also obtained if other liquid-crystal mixtures are employed, for example those described in pages 12-15.

EXAMPLE 2

(a) 6.8 g of 1-amino-2-(4,5-dihydrooxazol-2-yl)-4-nitroanthraquinone and 2.7 g of anhydrous potassium carbonate are introduced into 50 cc of N-methylpyrrolidone, 3.7 g of 4-tert.-butylthiophenyl are added to the mixture, and the latter is heated to 80° C. in the course of 1 hour and is kept at this temperature until the orange-red starting material has reacted completely. The reaction mixture is then diluted at 70° C. with 50 cc of methanol and is allowed to cool to room temperature. The dyestuff which has crystallised out is filtered off with suction, washed with methanol and hot water and dried at 60° C. This gives 6.9 g (corresponding to 75% of theory) of 1-amino-(2-(4,5-dihydrooxazol-2-yl)-4-(4-tert.-butylphenylmercapto)-anthraquinone, which is recrystallised from 100 cc of dimethylformamide and washed with ethanol.

The colour shade of the dyestuff when adsorbed onto silica gel is a bluish-tinged violet which is between Indicator Numbers 12 and 13 (CIHIC).

(b) In a 0.5% strength, bluish-tinged violet solution of the dyestuff described above in one of the liquid-crystal phases of Examples 1b or 1c, the dyestuff has an order parameter S of 0.75. Similar good order parameters are also obtained if other liquid-crystal mixtures are employed, for example those described on pages 12-15.

(c) The 1-amino-2-(4,5-dihydrooxazol-2-yl)-4-nitroanthraquinone employed in Example 2a can be prepared as follows:

34 g of 1-amino-4-nitroanthraquinone-2-carboxylic acid N-(2-methoxyethyl)-amide, prepared from 1-amino-4-nitroanthraquinone-2-carboxylic acid chloride and 2-methoxyethylamine, are introduced in 400 cc of 100% strength sulphuric acid, and the solution is warmed at 50° C. until cyclisation is complete. After cooling, the reaction mixture is poured onto 3 kg of ice, and the product is filtered off with suction and washed until neutral. The dry substance weighs 22 g, corresponding to a yield of 70% of theory. It is recrystallised from dimethylformamide.

EXAMPLE 3

(a) 14 g of 1-amino-2-(5,6-dihydro-4H-1,3-oxazin-2-yl)-4-nitroanthraquinone, 5.4 g of potassium carbonate, 100 cc of N-methylpyrrolidone and 5.9 g of 4-chlorothiophenol are reacted as in Example 2. The reaction mixture is worked up as described in that example to give 9.2 g of 1-amino-2-(5,6-dihydro-4H-1,3-oxazin-2-yl)-4-(4-chlorophenylmercapto)-anthraquinone, corresponding to a yield of 51% of theory.

The colour shade of the dyestuff when adsorbed onto silica gel is a bluish-tinged violet which is between Indicator Numbers 12 and 13.

(b) In one of the liquid-crystal phases of Examples 1b or 1c, the dyestuff described above has a blue-violet colour in solution and an order parameter S of 0.73.

(c) The 1-amino-2-(5,6-dihydro-4H-1,3-oxazin-2-yl)-4-nitroanthraquinone employed in Example 2a can be prepared from 1-amino-4-nitroanthraquinone-2-carboxylic acid N-(3-methoxypropyl)-amide analogously to the instructions in Example 2c.

EXAMPLE 4

(a) 4.1 g of 4-methylthiophenol are added to a suspension of 11.6 g of phenyl 1-amino-4-nitroanthraquinone-2-carboxylate, prepared from 1-amino-4-nitroanthraquinone-2-carboxylic acid chloride and phenol, and 4.2 g of potassium carbonate (anhydrous) in 50 cc of N-methylpyrrolidone, and the mixture is stirred at 80° C. until the starting material has reacted completely. The reaction mixture is diluted at 40° C. with 20 cc of water. After cooling to room temperature, the crystals which have separated out are filtered off with suction, washed with a mixture of N-methylpyrrolidone and water and then with hot water and dried at 60° C. This gives 7.2 g (corresponding to 53% of theory) of phenyl 1-amino-4-(4-methylphenylmercapto)-anthraquinone-2-carboxylate, which can be purified by recrystallisation from dimethylformamide.

The colour shade of the dyestuff when adsorbed onto silica gel is a bluish-tinged violet which is between Indicator Numbers 12 and 13 (CIHIC).

(b) A 0.5% strength solution of the dyestuff described above in one of the liquid-crystal phases of Examples 1b or 1c has a bluish-tinged violet colour. The order parameter S of the dyestuff is found to be 0.75 or 0.74.

Similar good order parameters are also obtained in other liquid-crystal mixtures, for example those described on pages 12-15.

EXAMPLE 5

(a) 11.6 g of phenyl 1-amino-4-nitroanthraquinone-2-carboxylate (see Example 3a), 4.2 g of potassium carbonate (anhydrous) and 4.8 g of 4-chlorothiophenol are introduced into 50 cc of N-methylpyrrolidone, and the mixture is heated at 80° C. until the starting material has reacted completely. The mixture is then diluted at 70° C. with 50 cc of methanol and is allowed to cool. The crystals which have separated out are filtered off with suction, washed with methanol and hot water and dried. This gives 8.3 g, corresponding to 65% of theory, of methyl 1-amino-4-(4-chlorophenylmercapto)-anthraquinone-2-carboxylate, which has been formed by reacting the phenyl ester with the methanol used for the precipitation. The dyestuff can be purified by recrystallisation from dimethylformamide.

The colour shade of the dyestuff when adsorbed onto silica gel is a bluish-tinged violet which is between Indicator Numbers 12 and 13 (CIHIC).

(b) In one of the liquid-crystal phases of Examples 1b or 1c, the dyestuff described above has a bluish-tinged violet colour in solution and an order parameter S of 0.74.

EXAMPLE 6

(a) 7.7 g of pentyl 1-amino-4-nitroanthraquinone-2-carboxylate, prepared from 1-amino-4-nitroanthraquinone-2-carboxylic acid chloride and n-pentanol, 2.7 g of anhydrous potassium carbonate and 2.7 g of 4-methylthiophenol are introduced into 50 cc of N-methylpyrrolidone, and the mixture is heated to 125°-130° C. in the course of 1 hour and is stirred at this temperature until, after about 1.5 hours, complete reaction has been achieved. The reaction mixture is allowed to cool and is diluted at 40° C. with 20 cc of water. When the mixture has cooled completely, the dyestuff which has been precipitated is filtered off with suction and washed with a mixture of N-methylpyrrolidone and water and then with hot water. After drying at 60° C., 6.7 g of n-pentyl 1-amino-4-(4-methylphenylmercapto)-anthraquinone-2-carboxylate are obtained, corresponding to a yield of 72% of theory. The dyestuff can be purified by recrystallisation from dimethylformamide.

The colour shade of the dyestuff when adsorbed onto silica gel is a bluish-tinged violet which is between Indicator Numbers 12 and 13 (CIHIC).

(b) When dissolved in one of the liquid-crystal phases of Examples 1b or 1c, the dyestuff described above has an order parameter S of 0.74. The solution has a blue-violet colour.

EXAMPLE 7

(a) If the 4-methylthiophenol in Example 5 is replaced by 4.9 g of n-pentyl 3-mercaptobenzoate, prepared analogously to the instructions of P. F. Wiley (J. Org. Chem. 16, (1951), 812) for the methyl and ethyl esters, the procedure otherwise being as described in that example, 6.1 g of n-pentyl 1-amino-4-(3-pentoxycarbonylphenylmercapto)-anthraquinone-2-carboxylate, corresponding to a yield of 54% of theory, are obtained after a reaction time of 3 hours at 125°-130° C. and appropriate working up.

The colour shade of the dyestuff when adsorbed onto silica gel is a bluish-tinged violet which is between Indicator Numbers 12 and 13 (CIHIC).

(b) The dyestuff described above imparts a blue-violet colour to a liquid-crystal phase such as was used in Examples 1b or 1c, and, in these phases, has an order parameter S of 0.74.

(c) n-Pentyl 1-amino-4-(4-methoxycarbonylphenylmercapto)-anthraquinone-2-carboxylate, which is readily soluble in the liquid-crystal phases of Examples 1b or 1c, giving a blue-violet colour, and has an order parameter S of 0.74 in these phases, is obtained entirely analogously to the procedure described in (a) from methyl 4-mercaptobenzoate, which is also described by P. F. Wiley (J. Org. Chem. 16 (1951), 813), but which can also be synthesized from the 4-mercaptobenzoic acid prepared by S. Smiles and D. C. Harrison (J. Chem. Soc. (London) 121 (1922), 2024) (in this connection see also the communication from D. Bramley and N. H. Chamberlain in J. Chem. Soc. (London) 1942, 376).

EXAMPLE 8

(a) 7.8 g of n-propyl 1-amino-4-bromoanthraquinone-2-carboxylate, 2.7 g of anhydrous potassium carbonate and 3.7 g of 4-tert.-butylthiophenol are introduced into 50 cc of N-methylpyrrolidone, and the mixture is heated to 125°-130° C. in the course of 1 hour. The reaction mixture is stirred at this temperature until the starting material has reacted, and is then diluted at 40° C. with 20 cc of water. When the mixture has cooled completely, it is filtered with suction and the product is washed with a mixture of N-methylpyrrolidone and water and then with hot water, and dried at 60° C. This gives 5.5 g of n-propyl 1-amino-4-(4-tert.-butylphenylmercapto)-anthraquinone-2-carboxylate, corresponding to a yield of 57% of theory.

The colour shade of the dyestuff when adsorbed onto silica gel is a bluish-tinged violet which is between Indicator Numbers 12 and 13 (CIHIC).

(b) The dyestuff described above imparts a blue-violet colour to a liquid-crystal phase such as was used in Examples 1b or 1c, and has an order parameter S of 0.71 in these phases. Similar good order parameters are also obtained in other liquid-crystal mixtures, for example those described on pages 12-15.

EXAMPLE 9

(a) If the 4-methylthiophenol in Example 4 is replaced by 6.2 g of 4-phenylthiophenol, prepared from 4-biphenylsulphonic acid, which is known from the literature, by converting the latter into the sulphonyl chloride and reducing this by the method of A. W. Wagner (Chem. Ber. 99, (1966), 375) using red phosphorus and iodine in glacial acetic acid, the procedure otherwise being as described above, after appropriate working up, 9.5 g of phenyl 1-amino-4-(4-biphenylmercapto)-anthraquinone-2-carboxylate (60% of theory) are obtained; this can be purified by recrystallisation from dimethylformamide.

The colour shade of the dyestuff when adsorbed onto silica gel is a bluish-tinged violet which is between Indicators Numbers 12 and 13 (CIHIC).

(b) In one of the liquid-crystal phases of Examples 1b or 1c, the dyestuff described above has a blue-violet colour in solution and an order parameter S of 0.78.

EXAMPLE 10

(a) 4.5 g of phenyl 1-amino-4,5,8-trichloroanthraquinone-2-carboxylate and 2 g of anhydrous potassium carbonate are introduced into 100 cc of dimethylformamide, 4 g of 4-methylthiophenol are added, and the mixture is then heated to 80° C. under a gentle stream of nitrogen and is kept at this temperature until the reaction is complete. The reaction mixture is then diluted at 40° C. with 40 cc of water, is allowed to cool completely and is filtered with suction, and the product is washed with a mixture of dimethylformamide and water and then with water. After drying at 60° C., 4.8 g of phenyl 1-amino-4,5,8-tri-(4-methylphenylmercapto)-anthraquinone-2-carboxylate are obtained, corresponding to a yield of 67% of theory.

The colour shade of the dyestuff when adsorbed onto silica gel is a reddish-tinged blue which is between Indicator Numbers 13 and 14 (CIHIC).

(b) The dyestuff described above imparts a blue colour to a liquid-crystal phase such as was used in Examples 1b or 1c, and has an order parameter S of 0.81 in this phase.

(c) The phenyl 1-amino-4,5,8-trichloroanthraquinone-2-carboxylate employed in Example 10a had been prepared as follows:

A mixture of 60 g of phenol and 4 g of anhydrous potassium carbonate is subjected to incipient vacuum distillation, in the course of which approx. 20 g of phenol and water are removed by distillation. 15.6 g of 1-amino-4,5,8-trichloroanthraquinone-2-carboxylic acid chloride, prepared from 1-amino-4,5,8-trichloroanthraquinone-2-carboxylic acid, described in German Auslegeschrift No. 1,154,490, Example 15, and excess thionyl chloride, are introduced to the cold melt, and the mixture is then heated at 60° C. for 30 minutes. It is then diluted at about 40° C. with 20 cc of water, is allowed to cool completely and is filtered with suction, and the product is washed with water and dried. This gives 12.2 g of the product, corresponding to a yield of 68% of theory.

(d) Pentyl 1-amino-4,5,8-tri-(4-methylphenylmercapto)-anthraquinone-2-carboxylate, which is also soluble in the liquid-crystal phases used in Example 1b or 1c, producing a reddish-tinged blue colour, and which has an order parameter of 0.79 therein, is obtained, entirely analogously to the procedure described under (a), from the analogous pentyl ester, prepared in accordance with

(c) from pentanol and 1-amino-4,5,8-trichloroanthraquinon-2-carboxylic acid chloride.

EXAMPLE 11

(a) 7.9 g of 1-amino-4-nitroanthraquinone-2-carboxylic acid N-(n-hexyl)-amide and 2.7 g of anhydrous potassium carbonate are introduced into 50 cc of N-methylpyrrolidone, 2.7 g of 4-methylthiophenol are added, and the mixture is heated at 80° C. until the reaction is complete. The mixture is then diluted at 70° C. with 50 cc of methanol, is allowed to cool and is filtered with suction, and the product is washed with methanol and water. This gives 6.0 g of 1-amino-4-(4-methylphenylmercapto)-anthraquinone-2-carboxylic acid N-(n-hexyl)-amide, corresponding to a yield of 63% of theory.

The colour shade of the dyestuff when adsorbed onto silica gel is a violet which is between Indicator Numbers 11 and 12 (CIHIC).

(b) The dyestuff described above imparts a violet colour to a liquid-crystal phase such as was used in Examples 1b or 1c, and has an order parameter S of 0.75 in this phase.

(c) The 1-amino-4-nitroanthraquinone-2-carboxylic acid N-(n-hexyl)-amide employed in Example 11a can be prepared from 1-amino-4-nitroanthraquinone-2-carboxylic acid by reacting the latter with excess thionyl chloride, distilling off the thionyl chloride and reacting the distillation residue with n-hexylamine.

EXAMPLE 12

1,4-Dichloroanthraquinone-6-carboxylic acid, which is described in Houben-Weyl, Methoden der organischen Chemie ["Methods of Organic Chemistry"], 4th Edition, 1979, G. Thieme Verlag, Stuttgart, Volume 7/3C, page 261, can also be converted, entirely analogously to the process described in Example 10, via its acid chloride into the corresponding n-pentyl ester or phenyl ester or a carboxamide, for example N-(n-hexyl)-carboxamide. The two chlorine atoms are then replaced by arylmercapto radicals in the manner described. This gives red compounds having the following order parameters:

(a) n-Pentyl 1,4-di-(4-chlorophenylmercapto)-anthraquinone-6-carboxylate, S=0.76

(b) Phenyl 1,4-diphenylmercaptoanthraquinone-6-carboxylate, S=0.75

(c) 1,4-Di-(4-methylphenylmercapto)-anthraquinone-6-carboxylic acid N-(n-hexyl)-amide, S=0.78

(d) 1,4-Di-(4-methylphenylmercapto)-anthraquinone-6-carboxylic acid anilide, S=0.79.

Further examples are listed in Table 2 which follows. The table relates to dyestuffs of the formula ##STR8##

In this formula, Q indicates the β-substituents; X in the table designates the position in which Q is attached to the anthraquinone ring, that is to say the 2-, 3-, 6- or 7-position.

The order parameter in the nematic phases of Examples 1b or 1c is indicated in columns S₁, S₂, S₃ and S₄. The data are determined in a 0.5% strength solution at a layer thickness of 23 μm, and are evaluated in accordance with the known procedure (for example British Patent Specification No. 2,071,685). The order parameters indicated in the table have the following meanings

in column S₁, they relate to dyestuffs in which Ar denotes phenyl;

in column S₂, they relate to dyestuffs in which Ar denotes 4-chlorophenyl;

in column S₃ they relate to dyestuffs in which Ar denotes 4-methylphenyl; and

in column S₄, they relate to dyestuffs in which Ar denotes 4-tert.-butylphenyl.

Under the heading Q, C₆ H₅ represents phenyl, C₆ H₄ represents phenylene, C₃ H₇ represents n-propyl, C₄ H₉ represents n-butyl and C₅ H₁₁ represents n-pentyl.

The numbers marked with dashes and placed in brackets denote the position, on the phenoxy radical, of the following substituent.

                                      TABLE 2     __________________________________________________________________________     Y'     Y"  Y"' X Q              S.sub.1                                        S.sub.2                                           S.sub.3                                              S.sub.4     __________________________________________________________________________     1  SAr SAr SAr (2)                      CH.sub.3          0.73                                           0.72     2  SAr SAr SAr (2)                      CH.sub.2 CH(CH.sub.3).sub.2                                     0.68                                        0.79                                           0.78                                              0.74     3  SAr SAr SAr (2)                      2-Oxazolinyl   0.68                                        0.79                                           0.78                                              0.74     4  SAr SAr SAr (2)                      CONHC.sub.6 H.sub.5                                     0.69                                        0.79                                           0.78                                              0.74     5  SAr SAr SAr (2)                      COOCH.sub.3    0.66                                        0.77                                           0.76                                              0.72     6  SAr SAr SAr (2)                      COOC.sub.3 H.sub.7                                        0.75                                           0.74     7  SAr SAr SAr (2)                      COOC.sub.5 H.sub.11                                        0.76                                           0.75                                              0.71     8  SAr SAr SAr (2)                      COOC.sub.6 H.sub.5                                     0.71                                        0.81                                           0.80                                              0.76     9  SAr SAr SAr (2)                      COOC.sub.6 H.sub.4 (4')CH.sub.3                                     0.72                                        0.81                                           0.81                                              0.77     10 SAr SAr SAr (2)                      COOC.sub.6 H.sub.4 (4')OCH.sub.3                                     0.72                                        0.82                                           0.81                                              0.77     11 SAr SAr SAr (2)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.71                                        0.81                                           0.80                                              0.76     12 SAr SAr SAr (2)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.73                                        0.82                                           0.82                                              0.78     13 SAr SAr SAr (2)                      OCH.sub.3            0.72     14 SAr SAr SAr (2)                      OC.sub.4 H.sub.9  0.75                                           0.74                                              0.69     15 SAr SAr SAr (2)                      OCH.sub.2 C.sub.6 H.sub.5                                        0.75                                           0.74                                              0.69     16 SAr SAr SAr (2)                      O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                     0.65                                        0.76                                           0.76                                              0.71     17 SAr SAr SAr (2)                      OC.sub.6 H.sub.5                                     0.69                                        0.79                                           0.79                                              0.75     18 SAr SAr SAr (2)                      OC.sub.6 H.sub.4 (2')Cl                                     0.70                                        0.80                                           0.79                                              0.75     19 SAr SAr SAr (2)                      OC.sub.6 H.sub.4 (3')Cl                                     0.71                                        0.80                                           0.80                                              0.76     20 SAr SAr SAr (2)                      OC.sub.6 H.sub.4 (3')F                                     0.70                                        0.80                                           0.79                                              0.75     21 SAr SAr SAr (2)                      OC.sub.6 H.sub.4 (4')CH.sub.3                                     0.70                                        0.80                                           0.79                                              0.75     22 SAr SAr SAr (2)                      OC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.71                                        0.81                                           0.80                                              0.76     23 SAr SAr SAr (2)                      OC.sub.6 H.sub.4 (4')SCH.sub.3                                     0.69                                        0.79                                           0.79                                              0.75     24 SAr SAr SAr (2)                      OC.sub.6 H.sub.4 (4')COOC.sub.2 H.sub.5                                     0.69                                        0.79                                           0.79                                              0.75     25 SAr SAr SAr (2)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.69                                        0.79                                           0.78                                              0.74     26 SAr SAr SAr (2)                      OC.sub.6 H.sub.4 (4')Cl                                     0.69                                        0.79                                           0.78                                              0.74     27 SAr SAr SAr (2)                      O2-Naphthyl       0.80                                           0.80                                              0.76     28 SAr SAr SAr (2)                      CN             0.62                                        0.74  0.68     29 SAr SAr SAr (2)                      Br                0.74  0.68     30 SAr SAr SAr (2)                      Cl                0.73     31 SAr SAr NH.sub.2                    (7)                      CH.sub.3       0.69                                        0.77                                           0.76                                              0.73     32 SAr SAr NH.sub.2                    (7)                      2-Oxazolinyl      0.81                                           0.81                                              0.78     33 SAr SAr NH.sub.2                    (7)                      CONHC.sub.6 H.sub.5                                     0.75                                        0.82                                           0.81     34 SAr SAr NH.sub.2                    (7)                      COOC.sub.5 H.sub.11                                        0.79  0.76     35 SAr SAr NH.sub.2                    (7)                      COOC.sub.6 H.sub.5                                     0.77                                        0.82  0.81     36 SAr SAr NH.sub.2                    (7)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                     0.78                                        0.82                                           0.82                                              0.81     37 SAr SAr NH.sub.2                    (7)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.77                                        0.82                                           0.82                                              0.80     38 SAr SAr NH.sub.2                    (7)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.79                                        0.83                                           0.82                                              0.82     39 SAr SAr NH.sub.2                    (7)                      OC.sub.4 H.sub.9                                     0.71  0.78                                              0.75     40 SAr SAr NH.sub.2                    (7)                      O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                        0.80                                           0.79                                              0.76     41 SAr SAr NH.sub.2                    (7)                      OC.sub.6 H.sub.5                                     0.76                                        0.82                                           0.82                                              0.79     42 SAr SAr NH.sub.2                    (7)                      OC.sub.6 H.sub.4 (4')OCH.sub.3                                     0.77                                        0.82                                           0.82                                              0.80     43 SAr SAr NH.sub.2                    (7)                      OC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.77                                        0.82                                           0.82     44 SAr SAr NH.sub.2                    (7)                      OC.sub.6 H.sub.4 (4') COOC.sub.5 H.sub.11                                        0.82                                           0.81                                              0.79     45 S Ar            SAr NH.sub.2                    (7)                      CN                0.77                                           0.77     46 SAr SAr NH.sub.2                    (2)                      CH.sub.2 CH(CH.sub.3).sub.2                                        0.82     47 SAr SAr NH.sub.2                    (2)                      CONHC.sub.6 H.sub.4 (4')CH.sub.3                                     0.75                                        0.82                                           0.81     48 SAr SAr NH.sub.2                    (2)                      COOC.sub.5 H.sub.11                                        0.79                                           0.79                                              0.76     49 SAr SAr NH.sub.2                    (2)                      COOC.sub.6 H.sub.5                                     0.77  0.82                                              0.81     50 SAr SAr NH.sub.2                    (2)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                        0.82                                           0.82     51 SAr SAr NH.sub.2                    (2)                      OC.sub.6 H.sub.5                                     0.76                                        0.82                                           0.82     52 SAr SAr NH.sub.2                    (2)                      OC.sub.6 H.sub.4 (3')F                                        0.82                                           0.82                                              0.80     53 SAr SAr NH.sub.2                    (2)                      OC.sub.6 H.sub.4 (4')COOC.sub.2 H.sub.5                                     0.76                                        0.82     54 SAr SAr NH.sub.2                    (2)                      O2-Naphthyl       0.82                                           0.82                                              0.80     55 SAr SAr NH.sub.2                    (2)                      CN                0.77  0.74     56 SAr SAr NH.sub.2                    (2)                      Cl                0.77     57 SAr SAr NH.sub.2                    (3)                      CH.sub.3          0.77                                           0.76     58 SAr SAr NH.sub.2                    (3)                      2-Oxazolinyl      0.81     59 SAr SAr NH.sub.2                    (3)                      CONHC.sub.6 H.sub.5                                     0.75                                        0.82                                           0.81                                              0.79     60 SAr SAr NH.sub.2                    (3)                      COOC.sub.5 H.sub.11                                     0.72                                        0.79                                           0.79                                              0.76     61 SAr SAr NH.sub.2                    (3)                      COOC.sub.6 H.sub.5                                     0.77                                        0.82  0.81     62 SAr SAr NH.sub.2                    (3)                      OCH.sub.3      0.69                                        0.77                                           0.76     63 SAr SAr NH.sub.2                    (3)                      OC.sub.6 H.sub.5                                     0.76                                        0.82  0.79     64 SAr SAr NH.sub.2                    (3)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.82                                           0.81                                              0.79     65 SAr SAr NH.sub.2                    (3)                      CN                0.77     66 SAr SAr H   (2)                      CF.sub.3       0.69                                        0.78                                           0.77     67 SAr SAr H   (2)                      2-Oxazolinyl   0.74                                        0.81                                           0.80     68 SAr SAr H   (2)                      CONHC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.74                                        0.81                                           0.81                                              0.78     69 SAr SAr H   (2)                      COOC.sub.5 H.sub.11                                        0.78                                           0.78     70 SAr SAr H   (2)                      COOC.sub.6 H.sub.5                                     0.76                                        0.82                                           0.82                                              0.80     71 SAr SAr H   (2)                      COOC.sub.6 H.sub.4 (4')CH.sub.3                                     0.77                                        0.82                                           0.82                                              0.80     72 SAr SAr H   (2)                      COOC.sub.6 H.sub.4 (4')Cl                                        0.82                                           0.82                                              0.80     73 SAr SAr H   (2)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.82                                           0.82                                              0.80     74 SAr SAr H   (2)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.78                                        0.82                                           0.82                                              0.81     75 SAr SAr H   (2)                      OC.sub.4 H.sub.9  0.77  0.74     76 SAr SAr H   (2)                      OC.sub.6 H.sub.5                                     0.75                                        0.81                                           0.81                                              0.78     77 SAr SAr H   (2)                      OC.sub.6 H.sub.4 (2')Cl                                        0.82     78 SAr SAr H   (2)                      OC.sub.6 H.sub.4 (3')CH.sub.3                                           0.81     79 SAr SAr H   (2)                      OC.sub.6 H.sub.4 (3')F                                        0.82                                           0.81                                              0.79     80 SAr SAr H   (2)                      OC.sub.6 H.sub.4 (4')CH.sub.3                                        0.82                                           0.81                                              0.79     81 SAr SAr H   (2)                      OC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.76                                        0.82                                           0.82     82 SAr SAr H   (2)                      OC.sub.6 H.sub.4 (4')COOC.sub.2 H.sub.5                                     0.75  0.81     83 SAr SAr H   (2)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.81  0.78     84 SAr SAr H   (2)                      O 2-Naphthyl   0.76                                        0.82  0.79     85 SAr SAr H   (2)                      CN                0.76                                           0.76                                              0.73     86 SAr SAr H   (2)                      Cl                   0.75     87 SAr SAr H   (3)                      CH.sub.2 CH(CH.sub.3).sub.2                                        0.81  0.78     88 SAr SAr H   (3)                      COOC.sub.5 H.sub.11                                     0.71  0.78                                              0.75     89 SAr SAr H   (3)                      COOC.sub.6 H.sub.5                                     0.76                                        0.82                                           0.82     90 SAr SAr H   (3)                      COOC.sub.6 H.sub.4 (4')Cl                                     0.76                                        0.82  0.80     91 SAr SAr H   (3)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.82                                           0.82                                              0.80     92 SAr SAr H   (3)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.78                                        0.82  0.81     93 SAr SAr H   (3)                      OCH.sub.3         0.76                                           0.75     94 SAr SAr H   (3)                      O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                        0.79                                           0.78                                              0.75     95 SAr SAr H   (3)                      OC.sub.6 H.sub.5                                     0.75  0.81     96 SAr SAr H   (3)                      OC.sub.6 H.sub.4 (2')Cl                                        0.82     97 SAr SAr H   (3)                      OC.sub.6 H.sub.4 (3')F                                     0.75                                        0.82                                           0.81     98 SAr SAr H   (3)                      OC.sub.6 H.sub.4 (4')CH.sub.3                                        0.82                                           0.81                                              0.79     99 SAr SAr H   (3)                      OC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.76                                        0.82                                           0.82     100        SAr SAr H   (3)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.74                                        0.81  0.78     101        SAr SAr H   (3)                      OC.sub.6 H.sub.4 (4')Cl                                        0.81                                           0.81                                              0.78     102        SAr SAr H   (3)                      CN                0.76     103        SAr SAr H   (3)                      Br                0.76                                           0.76                                              0.73     104        SAr SAr H   (6)                      2-Oxazolinyl      0.81                                           0.80                                              0.77     105        SAr SAr H   (6)                      CONHC.sub.6 H.sub.4 (3')F                                        0.81                                           0.81                                              0.78     106        SAr SAr H   (6)                      COOC.sub.5 H.sub.11                                        0.78  0.75     107        SAr SAr H   (6)                      COOC.sub.6 H.sub.5                                     0.76                                        0.82                                           0.82                                              0.80     108        SAr SAr H   (6)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                     0.77                                        0.82  0.80     109        SAr SAr H   (6)                      COOC.sub. 6 H.sub.4 (3')COOC.sub.5 H.sub.11                                     0.76                                        0.82                                           0.82     110        SAr SAr H   (6)                      CN                0.76     111        SAr NH.sub.2                NH.sub.2                    (2)                      CH.sub.3          0.76     112        SAr NH.sub.2                NH.sub.2                    (2)                      2-Oxazolinyl      0.81                                           0.81                                              0.79     113        SAr NH.sub.2                NH.sub.2                    (2)                      CONHC.sub.6 H.sub.5                                     0.77                                        0.82  0.80     114        SAr NH.sub.2                NH.sub.2                    (2)                      COOC.sub.5 H.sub.11                                        0.79                                           0.78                                              0.76     115        SAr NH.sub.2                NH.sub.2                    (2)                      COOC.sub.6 H.sub.5                                     0.79                                        0.82  0.81     116        SAr NH.sub.2                NH.sub.2                    (2)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                     0.79                                        0.82                                           0.82     117        SAr NH.sub.2                NH.sub.2                    (2)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.79                                        0.82                                           0.82     118        SAr NH.sub.2                NH.sub.2                    (2)                      O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                        0.79                                           0.79                                              0.77     119        SAr NH.sub.2                NH.sub.2                    (2)                      OC.sub.6 H.sub.5  0.82                                           0.81                                              0.80     120        SAr NH.sub.2                NH.sub.2                    (2)                      OC.sub.6 H.sub.4 (3')F                                           0.82                                              0.80     121        SAr NH.sub.2                NH.sub.2                    (2)                      OC.sub.6 H.sub.4 (4')CH.sub.3                                     0.78                                        0.82     122        SAr NH.sub.2                NH.sub.2                    (2)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.77                                        0.82                                           0.81     123        SAr NH.sub.2                NH.sub.2                    (2)                      CN                   0.77                                              0.75     124        SAr NH.sub.2                NH.sub.2                    (6)                      CH.sub.3       0.71                                        0.76                                           0.76                                              0.74     125        SAr NH.sub.2                NH.sub.2                    (6)                      CH.sub.2 CH(CH.sub.3).sub.2                                        0.61                                           0.81                                              0.79     126        SAr NH.sub.2                NH.sub.2                    (6)                      2-Oxazolinyl   0.77                                        0.81                                           0.81                                              0.79     127        SAr NH.sub.2                NH.sub.2                    (6)                      CONHC.sub.6 H.sub.5                                     0.77                                        0.82  0.80     128        SAr NH.sub.2                NH.sub.2                    (6)                      COOC.sub.3 H.sub.7                                     0.73                                        0.78  0.75     129        SAr NH.sub.2                NH.sub.2                    (6)                      COOC.sub.5 H.sub.11                                     0.74                                        0.79                                           0.78                                              0.76     130        SAr NH.sub.2                NH.sub.2                    (6)                      COOC.sub.6 H.sub.5                                     0.79  0.82     131        SAr NH.sub.2                NH.sub.2                    (6)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                     0.79                                        0.82                                           0.82     132        SAr NH.sub.2                NH.sub.2                    (6)                      COOC.sub.6 H.sub.4 (4')CH.sub.3                                     0.80                                        0.82                                           0.82                                              0.82     133        SAr NH.sub.2                NH.sub.2                    (6)                      COOC.sub.6 H.sub.4 (4')OCH.sub.3                                        0.82                                           0.82                                              0.82     134        SAr NH.sub.2                NH.sub.2                    (6)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.79                                        0.82                                           0.82     135        SAr NH.sub.2                NH.sub.2                    (6)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.81                                        0.82                                           0.82                                              0.82     136        SAr NH.sub.2                NH.sub.2                    (6)                      OC.sub.4 H.sub.9                                     0.73                                        0.78                                           0.77                                              0.75     137        SAr NH.sub.2                NH.sub.2                    (6)                      OCH.sub.2 C.sub.6 H.sub.5                                     0.73                                        0.78                                           0.77                                              0.75     138        SAr NH.sub.2                NH.sub.2                    (6)                      OC.sub.6 H.sub.5                                     0.78                                        0.82  0.80     139        SAr NH.sub.2                NH.sub.2                    (6)                      OC.sub.6 H.sub.4 (2')OC.sub.2 H.sub.5                                        0.82                                           0.82                                              0.80     140        SAr NH.sub.2                NH.sub.2                    (6)                      OC.sub.6 H.sub.4 (2')Cl                                        0.82                                           0.82                                              0.80     141        SAr NH.sub.2                NH.sub.2                    (6)                      OC.sub.6 H.sub.4 (3')CH.sub.3                                     0.78                                        0.82                                           0.82                                              0.80     142        SAr NH.sub.2                NH.sub.2                    (6)                      OC.sub.6 H.sub.4 (3')Cl                                     0.79                                        0.82                                           0.82                                              0.81     143        SAr NH.sub.2                NH.sub.2                    (6)                      OC.sub.6 H.sub.4 (3')F                                     0.78                                        0.82                                           0.82                                              0.80     144        SAr NH.sub.2                NH.sub.2                    (6)                      OC.sub.6 H.sub.4 (4')CH.sub.3                                     0.78  0.82     145        SAr NH.sub.2                NH.sub.2                    (6)                      OC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.79  0.82     146        SAr NH.sub.2                NH.sub.2                    (6)                      OC.sub.6 H.sub.4 (4')COOC.sub.2 H.sub.5                                        0.82                                           0.82                                              0.80     147        SAr NH.sub.2                NH.sub.2                    (6)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.82                                           0.81                                              0.80     148        SAr NH.sub.2                NH.sub.2                    (6)                      OC.sub.6 H.sub.4 (4')Cl                                        0.82                                           0.81                                              0.80     149        SAr NH.sub.2                NH.sub.2                    (6)                      O2-Naphthyl          0.82                                              0.81     150        SAr NH.sub.2                NH.sub.2                    (6)                      CN             0.72                                        0.77                                           0.77     151        SAr NH.sub.2                NH.sub.2                    (6)                      Br             0.72                                        0.77                                           0.77     152        NH.sub.2            SAr NH.sub.2                    (2)                      CH.sub.2 CH(CH.sub.3).sub.2                                        0.82     153        NH.sub.2            SAr NH.sub.2                    (2)                      CONHC.sub.6 H.sub.4 (3')CH.sub.3                                        0.82  0.82     154        NH.sub.2            SAr NH.sub.2                    (2)                      COOC.sub.5 H.sub.11                                        0.81                                           0.80                                              0.79     155        NH.sub.2            SAr NH.sub.2                    (2)                      COOC.sub.6 H.sub. 5                                     0.81  0.83                                              0.82     156        NH.sub.2            SAr NH.sub.2                    (2)                      COOC.sub.6 H.sub.4 (3')F                                     0.81  0.83                                              0.82     157        NH.sub.2            SAr NH.sub.2                    (2)                      COOC.sub.6 H.sub.4 (4')CH.sub.3                                     0.82                                        0.83                                           0.83     158        NH.sub.2            SAr NH.sub.2                    (2)                      OCH.sub.2 C.sub.6 H.sub.5                                     0.75                                        0.80                                           0.80                                              0.78     159        NH.sub.2            SAr NH.sub.2                    (2)                      OC.sub.6 H.sub.5                                     0.80                                        0.82                                           0.82                                              0.82     160        NH.sub.2            SAr NH.sub.2                    (2)                      OC.sub.6 H.sub.4 (3')F                                        0.82     161        NH.sub.2            SAr NH.sub.2                    (2)                      OC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                           0.83                                              0.82     162        NH.sub.2            SAr NH.sub.2                    (2)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.80                                        0.82     163        NH.sub.2            SAr NH.sub.2                    (2)                      CN                0.79     164        NH.sub.2            SAr NH.sub.2                    (3)                      CH.sub.3          0.79                                           0.78     165        NH.sub.2            SAr NH.sub.2                    (3)                      2-Oxazolinyl      0.82                                           0.82                                              0.81     166        NH.sub.2            SAr NH.sub.2                    (3)                      CONHC.sub.6 H.sub.5                                     0.80                                        0.82                                           0.82                                              0.82     167        NH.sub.2            SAr NH.sub.2                    (3)                      COOCH.sub.3       0.82     168        NH.sub.2            S Ar                NH.sub.2                    (3)                      COOC.sub.5 H.sub.11                                        0.81                                           0.80                                              0.79     169        NH.sub.2            SAr NH.sub.2                    (3)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                     0.81  0.83                                              0.82     170        NH.sub.2            SAr NH.sub.2                    (3)                      COOC.sub.6 H.sub.4 (4')Cl                                     0.81                                        0.83  0.82     171        NH.sub.2            SAr NH.sub.2                    (3)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.81  0.82                                              0.82     172        NH.sub.2            SAr NH.sub.2                    (3)                      OC.sub.6 H.sub.5  0.82                                           0.82                                              0.82     173        NH.sub.2            SAr NH.sub.2                    (3)                      OC.sub.6 H.sub.4 (2')OC.sub.2 H.sub.5                                     0.80                                        0.82     174        NH.sub.2            SAr NH.sub.2                    (3)                      OC.sub.6 H.sub.4 (2')Cl                                     0.80                                        0.82                                           0.82     175        NH.sub.2            SAr NH.sub.2                    (3)                      OC.sub.6 H.sub.4 (3')CH.sub.3                                        0.82                                           0.82                                              0.82     176        NH.sub.2            SAr NH.sub.2                    (3)                      OC.sub.6 H.sub.4 (3')Cl                                     0.81  0.82     177        NH.sub.2            SAr NH.sub.2                    (3)                      OC.sub.6 H.sub.4 (3')F                                     0.80  0.82                                              0.82     178        NH.sub.2            SAr NH.sub.2                    (3)                      OC.sub.6 H.sub.4 (4')CH.sub.3                                     0.80                                        0.82  0.82     179        NH.sub.2            SAr NH.sub.2                    (3)                      OC.sub.6 H.sub.4 (4')OCH.sub.3                                     0.81  0.82     180        NH.sub.2            SAr NH.sub.2                    (3)                      OC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                        0.83  0.82     181        NH.sub.2            SAr NH.sub.2                    (3)                      OC.sub.6 H.sub.4 (4')COOC.sub.2 H.sub.5                                     0.80                                        0.82                                           0.82                                              0.82     182        NH.sub.2            SAr NH.sub.2                    (3)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.82     183        NH.sub.2            SAr NH.sub.2                    (3)                      OC.sub.6 H.sub.4 (4')Cl                                     0.80                                        0.82                                           0.82                                              0.82     184        NH.sub.2            SAr NH.sub.2                    (3)                      CN             0.75                                        0.79                                           0.79     185        NH.sub.2            SAr NH.sub.2                    (3)                      Br             0.75                                        0.79                                           0.79     186        SAr NH.sub.2                OH  (6)                      CH.sub.3          0.74                                           0.73                                              0.71     187        SAr NH.sub.2                OH  (6)                      COOC.sub.5 H.sub.11                                        0.76     188        SAr NH.sub.2                OH  (6)                      COOC.sub.6 H.sub.5                                     0.77                                        0.81                                           0.81                                              0.79     189        SAr NH.sub.2                OH  (6)                      COOC.sub.6 H.sub.4 (4')Cl                                     0.77                                        0.81                                           0.81                                              0.79     190        SAr NH.sub.2                OH  (6)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.77                                        0.81                                           0.81                                              0.79     191        SAr NH.sub.2                OH  (6)                      OC.sub.4 H.sub.9     0.75                                              0.73     192        SAr NH.sub.2                OH  (6)                      OC.sub.6 H.sub.5                                     0.75  0.79     193        SAr NH.sub.2                OH  (6)                      OC.sub.6 H.sub.4 (3')F                                        0.80  0.78     194        SAr NH.sub.2                OH  (6)                      OC.sub.6 H.sub.4 (4')CH.sub.3                                        0.80  0.78     195        SAr NH.sub.2                OH  (6)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.79     196        SAr NH.sub.2                OH  (6)                      CN                0.74                                           0.74     197        SAr NH.sub.2                OH  (2)                      CH.sub.3       0.68                                        0.74     198        SAr NH.sub.2                OH  (3)                      2-Oxazolinyl      0.79     199        SAr NH.sub.2                OH  (3)                      CONHC.sub.6 H.sub.5                                     0.75                                        0.79                                           0.79                                              0.77     200        SAr NH.sub.2                OH  (7)                      COOC.sub.5 H.sub.11                                        0.76                                           0.76                                              0.74     201        SAr NH.sub.2                OH  (2)                      COOC.sub.6 H.sub.5                                     0.77                                        0.81                                           0.81                                              0.79     202        SAr NH.sub.2                OH  (3)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                     0.77                                        0.81                                           0.81     203        SAr NH.sub.2                OH  (7)                      COOC.sub.6 H.sub.4 (4')Cl                                        0.81                                           0.81                                              0.79     204        SAr NH.sub.2                OH  (2)                      COOC.sub.6 H.sub.4 (4')COOC.sub. 5 H.sub.11                                           0.81                                              0.79     205        SAr NH.sub.2                OH  (7)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.79                                        0.82     206        SAr NH.sub.2                OH  (3)                      OC.sub.4 H.sub.9  0.75                                           0.75                                              0.73     207        SAr NH.sub.2                OH  (7)                      O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                     0.72  0.76                                              0.74     208        SAr NH.sub.2                OH  (2)                      OC.sub.6 H.sub.5                                     0.75  0.79                                              0.77     209        SAr NH.sub.2                OH  (3)                      OC.sub.6 H.sub.4 (3')CH.sub.3                                     0.75                                        0.80                                           0.79     210        SAr NH.sub.2                OH  (2)                      OC.sub.6 H.sub.4 (3')F                                        0.80                                           0.80                                              0.78     211        SAr NH.sub.2                OH  (7)                      OC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.77                                        0.81     212        SAr NH.sub.2                OH  (2)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.79     213        SAr NH.sub.2                OH  (2)                      CN                   0.74                                              0.72     214        NH.sub.2            SAr OH  (3)                      CH.sub.3          0.76                                           0.76                                              0.74     215        NH.sub.2            SAr OH  (3)                      2-Oxazolinyl      0.81                                           0.81     216        NH.sub.2            SAr OH  (3)                      CONHC.sub.6 H.sub.5                                     0.77                                        0.81     217        NH.sub.2            SAr OH  (3)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.82  0.81     218        NH.sub.2            SAr OH  (3)                      OC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                        0.82     219        NH.sub.2            SAr OH  (3)                      OC.sub.6 H.sub.4 (3')COOC.sub.5 H.sub.11                                        0.81                                           0.81                                              0.79     220        NH.sub.2            SAr OH  (3)                      CN                0.77     221        NH.sub.2            SAr OH  (3)                      Br                   0.76     222        NH.sub.2            SAr OH  (7)                      CH.sub.2 CH(CH.sub.3).sub.2                                        0.81     223        NH.sub.2            SAr OH  (7)                      CONHC.sub.6 H.sub.5  0.81     224        NH.sub.2            SAr OH  (7)                      COOC.sub.5 H.sub.11                                        0.79                                           0.78     225        NH.sub.2            SAr OH  (7)                      COOC.sub.6 H.sub.5                                        0.82                                           0.82     226        NH.sub.2            SAr OH  (7)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.81                                        0.82                                           0.82                                              0.82     227        NH.sub.2            SAr OH  (7)                      OC.sub.4 H.sub.9  0.78                                           0.77                                              0.75     228        NH.sub.2            SAr OH  (7)                      OC.sub.6 H.sub.5                                     0.77                                        0.82  0.80     229        NH.sub.2            SAr OH  (7)                      OC.sub.6 H.sub.4 (3')F                                     0.78  0.82                                              0.80     230        NH.sub.2            S Ar                OH  (7)                      OC.sub.6 H.sub.4 (4')SCH.sub.3                                        0.82                                           0.81     231        NH.sub.2            SAr OH  (7)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.81                                           0.81                                              0.79     232        NH.sub.2            SAr OH  (7)                      CN                0.77                                           0.76                                              0.74     233        NH.sub.2            SAr Cl  (3)                      CH.sub.3          0.75     234        NH.sub.2            SAr Cl  (3)                      COOC.sub.5 H.sub.11                                        0.78                                           0.77     235        NH.sub.2            SAr Cl  (3)                      COOC.sub.6 H.sub.5                                     0.78                                        0.82                                           0.82                                              0.80     236        NH.sub.2            SAr Cl  (2)                      COOC.sub.6 H.sub.4 (4')CH.sub.3                                        0.82     237        NH.sub.2            SAr Cl  (3)                      OC.sub.6 H.sub.5                                     0.77                                        0.81                                           0.81     238        NH.sub.2            SAr Cl  (2)                      OC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                           0.82     239        NH.sub.2            SAr Cl  (3)                      CN             0.71                                        0.76     240        SAr NH.sub.2                H   (6)                      CH.sub.3          0.75                                           0.75                                              0.73     241        SAr NH.sub.2                H   (6)                      2-Oxazolinyl   0.76                                        0.80                                           0.80                                              0.78     242        SAr NH.sub.2                H   (6)                      CONHC.sub.6 H.sub.5                                     0.76                                        0.81                                           0.80                                              0.79     243        SAr NH.sub.2                H   (6)                      COOCH.sub.3       0.79     244        SAr NH.sub.2                H   (6)                      COOC.sub.3 H.sub.7                                        0.77                                           0.76     245        SAr NH.sub.2                H   (6)                      COOC.sub.5 H.sub.11                                     0.73                                        0.78                                           0.77     246        SAr NH.sub.2                H   (6)                      COOC.sub.6 H.sub.5                                        0.82                                           0.82                                              0.80     247        SAr NH.sub.2                H   (6)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                     0.79  0.82                                              0.81     248        SAr NH.sub.2                H   (6)                      COOC.sub.6 H.sub.4 (4')CH.sub.3                                           0.82                                              0.81     249        SAr NH.sub.2                H   (6)                      COOC.sub.6 H.sub.4 (4')Cl                                     0.78                                        0.82                                           0.82     250        SAr NH.sub.2                H   (6)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.82                                           0.82                                              0.80     251        SAr NH.sub.2                H   (6)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.80                                        0.82                                           0.82     252        SAr NH.sub.2                H   (6)                      CN                0.76                                           0.76     253        SAr NH.sub.2                H   (6)                      Br                0.76     254        SAr NH.sub.2                H   (2)                      CH.sub.3          0.75                                           0.75                                              0.73     255        SAr NH.sub.2                H   (2)                      2-Oxazolinyl      0.80                                           0.80     256        SAr NH.sub.2                H   (2)                      CONHC.sub.6 H.sub.5                                     0.76                                        0.81     257        SAr NH.sub.2                H   (2)                      COOC.sub.5 H.sub.11                                        0.78  0.75     258        SAr NH.sub.2                H   (2)                      COOC.sub.6 H.sub.5   0.82                                              0.80     259        SAr NH.sub.2                H   (2)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                     0.79                                        0.82  0.81     260        SAr NH.sub.2                H   (2)                      COOC.sub.6 H.sub.4 (4')CH.sub.3                                        0.82                                           0.82                                              0.81     261        SAr NH.sub.2                H   (2)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.82                                           0.82     262        SAr NH.sub.3                H   (2)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                           0.82     263        SAr NH.sub.2                H   (2)                      OC.sub.6 H.sub.5                                     0.77                                        0.81                                           0.81                                              0.79     264        SAr NH.sub.2                H   (2)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.76                                        0.81  0.79     265        SAr NH.sub.2                H   (2)                      CN                0.76                                           0.76     266        SAr NH.sub.2                H   (3)                      CH.sub.2 CH(CH.sub.3).sub.2                                        0.80     267        SAr NH.sub.2                H   (3)                      2-Oxazolinyl   0.76                                        0.80  0.78     268        SAr NH.sub.2                H   (3)                      CONHC.sub.6 H.sub.5                                        0.81  0.79     269        SAr NH.sub.2                H   (3)                      COOC.sub.5 H.sub.11                                        0.78     270        SAr NH.sub.2                H   (3)                      COOC.sub. 6 H.sub.5                                        0.82  0.80     271        SAr NH.sub.2                H   (3)                      COOC.sub.6 H.sub.4 (4')CH.sub.3                                     0.79                                        0.82                                           0.82                                              0.81     272        SAr NH.sub.2                H   (3)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                        0.82     273        SAr NH.sub.2                H   (3)                      OC.sub.4 H.sub.9                                     0.72                                        0.77     274        SAr NH.sub.2                H   (3)                      OC.sub.6 H.sub.5                                     0.77                                        0.81                                           0.81                                              0.79     275        SAr NH.sub.2                H   (3)                      OC.sub.6 H.sub.4 (4')COOC.sub.2 H.sub.5                                        0.81  0.79     276        SAr NH.sub.2                H   (3)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.81                                           0.80     277        SAr NH.sub.2                H   (3)                      O2-Naphthyl       0.82     278        SAr NH.sub.2                H   (3)                      CN                0.76                                           0.76                                              0.74     279        NH.sub.2            H   SAr (3)                      CH.sub.3          0.72     280        NH.sub.2            H   SAr (3)                      2-Oxazolinyl      0.77                                           0.77                                              0.75     281        NH.sub.2            H   SAr (3)                      CONHC.sub.6 H.sub.5                                        0.78                                           0.78                                              0.76     282        NH.sub.2            H   SAr (3)                      COOCH.sub.3       0.76                                           0.75     283        NH.sub.2            H   SAr (3)                      COOC.sub.5 H.sub.11                                        0.75                                           0.74                                              0.72     284        NH.sub.2            H   SAr (3)                      COOC.sub.6 H.sub.5                                        0.80  0.78     285        NH.sub.2            H   SAr (3)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                     0.75                                        0.80                                           0.80     286        NH.sub.2            H   SAr (3)                      COOC.sub.6 H.sub.4 (4')CH.sub.3                                        0.80  0.78     287        NH.sub.2            H   SAr (3)                      COOC.sub.6 H.sub.4 (4')Cl                                        0.80                                           0.79     288        NH.sub.2            H   SAr (3)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.75     0.77     289        NH.sub.2            H   SAr (3)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.77                                        0.81  0.79     290        NH.sub.2            H   SAr (3)                      OCH.sub.2 C.sub.6 H.sub.5                                        0.74     291        NH.sub.2            H   SAr (3)                      OC.sub.6 H.sub.5  0.78                                           0.78                                              0.76     292        NH.sub.2            H   SAr (3)                      OC.sub.6 H.sub.4 (2')Cl                                        0.79                                           0.78     293        NH.sub.2            H   SAr (3)                      OC.sub.6 H.sub.4 (3')CH.sub.3                                     0.74                                        0.78  0.76     294        NH.sub.2            H   SAr (3)                      OC.sub.6 H.sub.4 (3')F                                     0.74                                        0.79                                           0.78     295        NH.sub.2            H   SAr (3)                      OC.sub.6 H.sub.4 (4')CH.sub.3                                     0.74                                        0.79  0.76     296        NH.sub.2            H   SAr (3)                      OC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                           0.79     297        NH.sub.2            H   SAr (3)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.78  0.76     298        NH.sub.2            H   SAr (3)                      CN                0.73  0.70     299        NH.sub.2            H   SAr (3)                      Cl                0.72     300        NH.sub.2            H   SAr (2)                      2-Oxazolinyl      0.77                                           0.77                                              0.75     301        NH.sub.2            H   SAr (2)                      CONHC.sub.6 H.sub.5                                        0.78     302        NH.sub.2            H   SAr (2)                      COOC.sub.5 H.sub.11                                        0.75     303        NH.sub.2            H   SAr (2)                      COOC.sub.6 H.sub.5                                        0.80                                           0.79                                              0.78     304        NH.sub.2            H   SAr (2)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                           0.80     305        NH.sub.2            H   SAr (2)                      O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                        0.75     306        NH.sub.2            H   SAr (2)                      OC.sub.6 H.sub.5                                     0.73                                        0.78                                           0.78                                              0.76     307        NH.sub.2            H   SAr (2)                      OC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                        0.80                                           0.79     308        NH.sub.2            H   SAr (2)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.78                                           0.78     309        NH.sub.2            H   SAr (2)                      CN                0.73                                           0.72     310        NH.sub.2            H   SAr (7)                      CH.sub.3       0.66                                        0.72                                           0.71                                              0.69     311        NH.sub.2            H   SAr (7)                      2-Oxazolinyl      0.77                                           0.77                                              0.75     312        NH.sub.2            H   SAr (7)                      CONHC.sub.6 H.sub.4 (4')CH.sub.3                                     0.73                                        0.78                                           0.78                                              0.76     313        NH.sub.2            H   SAr (7)                      COOCH.sub.3       0.76  0.73     314        NH.sub.2            H   SAr (7)                      COOC.sub.5 H.sub.11                                        0.75                                           0.74     315        NH.sub.2            H   SAr (7)                      COOC.sub.6 H.sub.5                                     0.75                                        0.80                                           0.79                                              0.78     316        NH.sub.2            H   SAr (7)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                     0.75                                        0.80  0.78     317        NH.sub.2            H   SAr (7)                      COOC.sub.6 H.sub.4 (4')CH.sub.3                                     0.76  0.80                                              0.78     318        NH.sub.2            H   SAr (7)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.80                                           0.79     319        NH.sub.2            H   SAr (7)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.77                                        0.81  0.79     320        NH.sub.2            H   SAr (7)                      CN                0.73                                           0.72                                              0.70     321        NH.sub.2            SAr H   (3)                      CH.sub.3       0.73                                        0.78                                           0.77     322        NH.sub.2            SAr H   (3)                      CH.sub.2 CH(CH.sub.3).sub.2                                        0.82                                           0.82     323        NH.sub.2            SAr H   (3)                      2-Oxazolinyl      0.82                                           0.82                                              0.80     324        NH.sub.2            SAr H   (3)                      CONHC.sub.6 H.sub.5                                     0.79                                        0.82  0.81     325        NH.sub.2            SAr H   (3)                      COOC.sub.3 H.sub.7                                        0.79                                           0.79     326        NH.sub.2            SAr H   (3)                      COOC.sub.5 H.sub.11                                     0.75                                        0.80                                           0.80     327        NH.sub.2            SAr H   (3)                      COOC.sub.6 H.sub.5                                     0.80                                        0.82  0.82     328        NH.sub.2            SAr H   (3)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                           0.82                                              0.82     329        NH.sub.2            SAr H   (3)                      COOC.sub.6 H.sub.4 (4')CH.sub.3                                     0.81                                        0.83                                           0.82                                              0.82     330        NH.sub.2            SAr H   (3)                      COOC.sub.6 H.sub.4 (4')OCH.sub.3                                        0.83     331        NH.sub.2            SAr H   (3)                      COOC.sub.6 H.sub.4 (4')Cl                                        0.82  0.82     332        NH.sub.2            SAr H   (3)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.80                                        0.82                                           0.82                                              0.82     333        NH.sub.2            SAr H   (3)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                           0.83     334        NH.sub.2            SAr H   (3)                      OC.sub. 4 H.sub.9 0.79  0.77     335        NH.sub.2            SAr H   (3)                      O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                     0.76  0.80     336        NH.sub.2            SAr H   (3)                      OC.sub.6 H.sub.5                                     0.79                                        0.82                                           0.82                                              0.81     337        NH.sub.2            SAr H   (3)                      OC.sub.6 H.sub.4 (2')Cl                                        0.82     338        NH.sub.2            SAr H   (3)                      OC.sub.6 H.sub.4 (3')CH.sub.3                                        0.82                                           0.82     339        NH.sub.2            SAr H   (3)                      OC.sub.6 H.sub.4 (3')F                                     0.79                                        0.82  0.81     340        NH.sub.2            SAr H   (3)                      OC.sub.6 H.sub.4 (4')CH.sub.3                                     0.79                                        0.82                                           0.82     341        NH.sub.2            SAr H   (3)                      OC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                        0.82                                           0.82                                              0.82     342        NH.sub.2            SAr H   (3)                      OC.sub.6 H.sub.4 (4')COOC.sub.2 H.sub.5                                           0.82                                              0.81     343        NH.sub.2            SAr H   (3)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.79                                        0.82                                           0.82                                              0.81     344        NH.sub.2            SAr H   (3)                      O2-Naphthyl       0.82  0.82     345        NH.sub.2            SAr H   (3)                      NO.sub.2          0.78     346        NH.sub.2            SAr H   (3)                      Br                   0.78     347        NH.sub.2            SAR H   (2)                      CH.sub.3          0.78     348        NH.sub.2            SAr H   (2)                      2-Oxazolinyl      0.82  0.80     349        NH.sub.2            SAr H   (2)                      CONHC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.79                                        0.82     350        NH.sub.2            SAr H   (2)                      COOC.sub.5 H.sub.11                                        0.80                                           0.80                                              0.78     351        NH.sub.2            SAr H   (2)                      COOC.sub.6 H.sub.5                                     0.80                                        0.82                                           0.82     352        NH.sub.2            SAr H   (2)                      O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                        0.80                                           0.80                                              0.78     353        NH.sub.2            SAr H   (2)                      OC.sub.6 H.sub.5                                     0.79                                        0.82  0.81     354        NH.sub.2            SAr H   (2)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.82     355        NH.sub.2            SAr H   (2)                      CN                   0.78     356        NH.sub.2            SAr H   (6)                      CH.sub.3          0.78  0.75     357        NH.sub.2            SAr H   (6)                      2-Oxazolinyl      0.82                                           0.82     358        NH.sub.2            SAr H   (6)                      CONHC.sub.6 H.sub.4 (3')Cl                                        0.82                                           0.82     359        NH.sub.2            SAr H   (6)                      COOC.sub.5 H.sub.11                                     0.75                                        0.80                                           0.80     360        NH.sub.2            SAr H   (6)                      COOC.sub.6 H.sub.5                                        0.82                                           0.82                                              0.82     361        NH.sub.2            SAr H   (6)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.80                                        0.82  0.82     362        NH.sub.2            SAr H   (6)                      CN                   0.78     363        NH.sub.2            SAr H   (6)                      Cl             0.73     364        OH  SAr OH  (3)                      CH.sub.3          0.73                                           0.73     365        OH  SAr OH  (3)                      CH.sub.2 CH(CH.sub.3).sub.2                                     0.74  0.79                                              0.77     366        OH  SAr OH  (3)                      2-Oxazolinyl   0.74  0.78     367        OH  SAr OH  (3)                      CONHC.sub.6 H.sub.5                                        0.79     368        OH  SAr OH  (3)                      COOC.sub.5 H.sub.11                                        0.76                                           0.76     369        OH  SAr OH  (3)                      COOC.sub.6 H.sub.5                                     0.77                                        0.81  0.79     370        OH  SAr OH  (3)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                     0.77  0.81     371        OH  SAr OH  (3)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                        0.82                                           0.82     372        OH  SAr OH  (3)                      OCH.sub.2 C.sub.6 H.sub.5                                        0.75     373        OH  SAr OH  (3)                      OC.sub.6 H.sub.5                                     0.75                                        0.79                                           0.79                                              0.77     374        OH  SAr OH  (3)                      OC.sub.6 H.sub.4 (3')Cl 0.78     375        OH  SAr OH  (3)                      OC.sub.6 H(4')C.sub.6 H.sub.5                                           0.81                                              0.79     376        OH  SAr OH  (3)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.79                                           0.79                                              0.77     377        OH  SAr OH  (3)                      CN                0.74     378        OH  SAr OH  (3)                      Cl                      0.71     379        OH  SAr H   (3)                      CH.sub.3       0.70                                        0.75  0.72     380        OH  SAr H   (3)                      COOC.sub.5 H.sub.11                                     0.73                                        0.78     381        OH  SAr H   (3)                      COOC.sub.6 H.sub.5                                        0.82                                           0.82     382        OH  SAr H   (3)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                        0.82     383        OH  SAr H   (3)                      OC.sub.6 H.sub.5                                     0.76                                        0.81                                           0.80                                              0.79     384        OH  SAr H   (3)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                           0.80     385        OH  SAr H   (3)                      CN                0.76                                           0.75     386        OH  SAr H   (2)                      CH.sub.2 CH(CH.sub.3).sub.2                                        0.80     387        OH  SAr H   (2)                      2-Oxazolinyl      0.80                                           0.80     388        OH  SAr H   (2)                      COOC.sub.3 H.sub.7   0.76                                              0.74     389        OH  SAr H   (2)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.                                     0.78                                        0.82                                           0.82     390        OH  SAr H   (2)                      OC.sub.4 H.sub.9  0.77                                           0.76     391        OH  SAr H   (2)                      OC.sub.6 H.sub.4 (3')F                                        0.81                                           0.81     392        OH  SAr H   (2)                      O2-Naphthyl          0.82     393        OH  SAr H   (2)                      CN                   0.75     394        OH  SAr H   (6)                      CH.sub.3          0.75     395        OH  SAr H   (6)                      2-Oxazolinyl      0.80                                           0.80                                              0.78     396        OH  SAr H   (6)                      CONHC.sub.6 H.sub.4 (3')F                                     0.76                                        0.81  0.79     397        OH  SAr H   (6)                      COOCH.sub.3       0.79                                           0.78     398        OH  SAr H   (6)                      COOC.sub.6 H.sub.4 (3')F                                        0.82                                           0.82                                              0.80     399        OH  SAr H   (6)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.80     0.82     400        Cl  SAr H   (2)                      CH.sub.3          0.74                                           0.74     401        Cl  SAr H   (6)                      COOC.sub.6 H.sub.5   0.81                                              0.80     402        SAr H   H   (2)                      CH.sub.3          0.74                                           0.74                                              0.71     403        SAr H   H   (2)                      CH.sub.2 CH(CH.sub.3).sub.2                                     0.75                                        0.80                                           0.79     404        SAr H   H   (2)                      2-Oxazolinyl   0.75                                        0.79                                           0.79     405        S Ar            H   H   (2)                      CONHC.sub.6 H.sub.5                                     0.75                                        0.80  0.78     406        SAr H   H   (2)                      COOC.sub.3 H.sub.7                                        0.76                                           0.75                                              0.73     407        SAr H   H   (2)                      COOC.sub.5 H.sub.11                                        0.77                                           0.76     408        SAr H   H   (2)                      COOC.sub.6 H.sub.5                                        0.82                                           0.81                                              0.80     409        SAr H   H   (2)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                        0.82                                           0.81                                              0.80     410        SAr H   H   (2)                      COOC.sub.6 H.sub.4 (4')CH.sub.3                                        0.82                                           0.82                                              0.80     411        SAr H   H   (2)                      COOC.sub.6 H.sub.4 (4')Cl                                     0.77                                        0.81                                           0.81     412        SAr H   H   (2)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.81                                           0.81     413        SAr H   H   (2)                      OC.sub.4 H.sub.9                                     0.71                                        0.76  0.73     414        SAr H   H   (2)                      O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                     0.72  0.77     415        SAr H   H   (2)                      OC.sub.6 H.sub.5                                     0.76  0.80     416        SAr H   H   (2)                      OC.sub.6 H.sub.5 (2')Cl                                        0.81                                           0.80                                              0.79     417        SAr H   H   (2)                      OC.sub.6 H.sub.4 (3')CH.sub.3                                     0.76                                        0.80                                           0.80     418        SAr H   H   (2)                      OC.sub.6 H.sub.4 (3')F                                        0.81                                           0.80                                              0.79     419        SAr H   H   (2)                      OC.sub.6 H.sub.4 (4')OCH.sub.3                                     0.77                                        0.81                                           0.81                                              0.79     420        SAr H   H   (2)                      OC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.77                                        0.82                                           0.81                                              0.80     421        SAr H   H   (2)                      OC.sub.6 H.sub.4 (4')COOC.sub.2 H.sub.5                                     0.76                                        0.80  0.78     422        SAr H   H   (2)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.75  0.80                                              0.78     423        SAr H   H   (2)                      O2-Naphthyl       0.81                                           0.81                                              0.79     424        SAr H   H   (2)                      CN             0.70                                        0.75                                           0.75                                              0.72     425        SAr H   H   (2)                      Cl                   0.74     426        H   H   SAr (2)                      CH.sub.3             0.63                                              0.60     427        H   H   SAr (2)                      CH.sub.2 CH(CH.sub.3).sub.2                                        0.70                                           0.70     428        H   H   SAr (2)                      2-Oxazolinyl      0.70     429        H   H   SAr (2)                      CONHC.sub.6 H.sub.5                                     0.65                                        0.71                                           0.70     430        H   H   SAr (2)                      COOC.sub.3 H.sub.7                                        0.65                                           0.64     431        H   H   SAr (2)                      COOC.sub.6 H.sub.5                                        0.73                                           0.73                                              0.70     432        H   H   SAr (2)                      COOC.sub.6 H.sub.4 (4')OCH.sub.3                                     0.69                                        0.74  0.71     433        H   H   SAr (2)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.73                                           0.72     434        H   H   SAr (2)                      CN                   0.64     435        H   SAr H   (2)                      CH.sub.3          0.77                                           0.76                                              0.74     436        H   SAr H   (2)                      CH.sub.2 CH(CH.sub.3).sub.2                                     0.77                                        0.82  0.80     437        H   SAr H   (2)                      2-Oxazolinyl      0.81                                           0.81                                              0.79     438        H   SAr H   (2)                      CONHC.sub.6 H.sub.5                                        0.82                                           0.82     439        H   SAr H   (2)                      COOC.sub.3 H.sub.7                                        0.78                                           0.78     440        H   SAr H   (2)                      COOC.sub.5 H.sub.11                                     0.74  0.79     441        H   SAr H   (2)                      COOC.sub.6 H.sub.5   0.82                                              0.82     442        H   SAr H   (2)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                        0.82                                           0.82                                              0.82     443        H   SAr H   (2)                      COOC.sub.6 H.sub.4 (4')OCH.sub.3                                     0.80  0.82                                              0.82     444        H   SAr H   (2)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.79                                        0.82  0.81     445        H   SAr H   (2)                      CN                0.77                                           0.77                                              0.75     446        H   SAr H   (2)                      Cl                0.77     447        NH.sub.2            NH.sub.2                NH.sub.2                    (2)                      CH.sub.3          0.72     448        NH.sub.2            NH.sub.2                NH.sub.2                    (3)                      2-Oxazolinyl      0.78                                           0.78                                              0.77     449        NH.sub.2            NH.sub.2                NH.sub.2                    (3)                      CONHC.sub.6 H.sub.5                                        0.79                                           0.78     450        NH.sub.2            NH.sub.2                NH.sub.2                    (7)                      COOC.sub.3 H.sub.7                                        0.74                                           0.74                                              0.73     451        NH.sub.2            NH.sub.2                NH.sub.2                    (6)                      COOC.sub.5 H.sub.11                                     0.73  0.75                                              0.74     452        NH.sub.2            NH.sub.2                NH.sub.2                    (6)                      COOC.sub.6 H.sub.5                                     0.78                                        0.80     453        NH.sub.2            NH.sub.2                NH.sub.2                    (7)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                        0.80  0.79     454        NH.sub.2            NH.sub.2                NH.sub.2                    (2)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.80     455        NH.sub.2            NH.sub.2                NH.sub.2                    (3)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                        0.82                                           0.82                                              0.81     456        NH.sub.2            NH.sub.2                NH.sub.2                    (3)                      OC.sub.6 H.sub.5  0.79                                           0.79                                              0.78     457        NH.sub.2            NH.sub.2                NH.sub.2                    (6)                      OC.sub.6 H.sub.4 (3')F                                        0.79  0.78     458        NH.sub.2            NH.sub.2                NH.sub.2                    (7)                      OC.sub.6 H.sub.4 (4')CH.sub.3                                        0.79                                           0.79                                              0.78     459        NH.sub.2            NH.sub.2                H   (2)                      CH.sub.3          0.71                                           0.71                                              0.70     460        NH.sub.2            NH.sub.2                H   (2)                      COOC.sub.5 H.sub.11                                        0.74  0.73     461        NH.sub.2            NH.sub.2                H   (2)                      COOC.sub.6 H.sub.5                                     0.77                                        0.79                                           0.79     462        NH.sub.2            NH.sub.2                H   (2)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                        0.81  0.80     463        NH.sub.2            NH.sub.2                H   (2)                      OC.sub.6 H.sub.5                                     0.75                                        0.78                                           0.78                                              0.77     464        NH.sub.2            NH.sub.2                H   (2)                      OC.sub.6 H.sub.4 (3')CH.sub.3                                        0.78  0.77     465        NH.sub.2            NH.sub.2                H   (3)                      CH.sub.3          0.71                                           0.71                                              0.70     466        NH.sub.2            NH.sub.2                H   (3)                      CH.sub.2 CH(CH.sub.3).sub.2                                        0.77     467        NH.sub.2            NH.sub.2                H   (3)                      2-Oxazolinyl      0.77  0.76     468        NH.sub.2            NH.sub.2                H   (3)                      CONHC.sub.6 H.sub.5                                     0.75                                        0.78                                           0.77                                              0.76     469        NH.sub.2            NH.sub.2                H   (3)                      COOCH.sub.3          0.75     470        NH.sub.2            NH.sub.2                H   (3)                      COOC.sub.5 H.sub.11                                        0.74                                           0.74                                              0.73     471        NH.sub.2            NH.sub.2                H   (3)                      COOC.sub.6 H.sub.5                                     0.77                                        0.79                                           0.79     472        NH.sub.2            NH.sub.2                H   (3)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                        0.80                                           0.79                                              0.79     473        NH.sub.2            NH.sub.2                H   (3)                      COOC.sub.6 H.sub.4 (4')Cl                                           0.79                                              0.78     474        NH.sub.2            NH.sub.2                H   (3)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.77                                        0.79     475        NH.sub.2            NH.sub.2                H   (3)                      OCH.sub.2 C.sub.6 H.sub.5                                        0.73  0.72     476        NH.sub.2            NH.sub.2                H   (3)                      OC.sub.6 H.sub.5                                     0.75                                        0.78                                           0.78                                              0.77     477        NH.sub.2            NH.sub.2                H   (3)                      OC.sub.6 H.sub.4 (2')OC.sub.2 H.sub.5                                     0.76  0.78                                              0.77     478        NH.sub.2            NH.sub.2                H   (3)                      OC.sub.6 H.sub.4 (3')CH.sub.3                                        0.78                                           0.78                                              0.77     479        NH.sub.2            NH.sub.2                H   (3)                      OC.sub.6 H.sub.4 (3')F                                     0.76                                        0.78                                           0.78     480        NH.sub.2            NH.sub.2                H   (3)                      OC.sub.6 H.sub.4 (4')CH.sub.3                                     0.76                                        0.78                                           0.78     481        NH.sub.2            NH.sub.2                H   (3)                      OC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.77                                        0.79                                           0.79     482        NH.sub.2            NH.sub.2                H   (3)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.75  0.77                                              0.76     483        NH.sub.2            NH.sub.2                H   (3)                      O2-Naphthyl          0.79     484        NH.sub.2            NH.sub.2                H   (3)                      CN                   0.72     485        NH.sub.2            NH.sub.2                H   (3)                      Cl                0.71     486        NH.sub.2            NH.sub.2                H   (6)                      CH.sub.3          0.71     487        NH.sub.2            NH.sub.2                H   (6)                      CONHC.sub.6 H.sub.5                                     0.75                                        0.78     488        NH.sub.2            NH.sub.2                H   (6)                      COOCH.sub.3    0.73                                        0.75                                           0.75     489        NH.sub.2            NH.sub.2                H   (6)                      COOC.sub.6 H.sub.5                                     0.77                                        0.79                                           0.79                                              0.78     490        NH.sub.2            NH.sub.2                H   (6)                      COOC.sub.6 H.sub.4 (4')Cl                                        0.79     491        NH.sub.2            NH.sub.2                H   (6)                      OC.sub.6 H.sub.5  0.78     492        NH.sub.2            NH.sub.2                H   (6)                      CN                   0.72     493        H   NH.sub.2                NH.sub.2                    (2)                      CH.sub.3          0.71                                           0.71     494        H   NH.sub.2                NH.sub.2                    (2)                      2-Oxazolinyl      0.77     495        H   NH.sub.2                NH.sub.2                    (2)                      CONHC.sub.6 H.sub.5                                        0.78                                           0.77     496        H   NH.sub.2                NH.sub.2                    (2)                      COOC.sub.3 H.sub.7                                     0.70                                        0.73                                           0.73     497        H   NH.sub.2                NH.sub.2                    (2)                      COOC.sub.5 H.sub.11  0.74                                              0.73     498        H   NH.sub.2                NH.sub.2                    (2)                      COOC.sub.6 H.sub.5                                     0.77                                        0.79                                           0.79                                              0.78     499        H   NH.sub.2                NH.sub.2                    (2)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                           0.79     500        H   NH.sub.2                NH.sub.2                    (2)                      COOC.sub.6 H.sub.4 (4')CH.sub.3                                           0.80     501        H   NH.sub.2                NH.sub.2                    (2)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                           0.79     502        H   NH.sub.2                NH.sub.2                    (6)                      CH.sub.2 CH(CH.sub.3).sub.2                                        0.77  0.76     503        H   NH.sub.2                NH.sub.2                    (6)                      2-Oxazolinyl      0.77                                           0.77     504        H   NH.sub.2                NH.sub.2                    (6)                      CONHC.sub.6 H.sub.5                                     0.75  0.77                                              0.76     505        H   NH.sub.2                NH.sub.2                    (6)                      COOC.sub.3 H.sub.7                                        0.73                                           0.73     506        H   NH.sub.2                NH.sub.2                    (6)                      COOC.sub.6 H.sub.5                                     0.77                                        0.79                                           0.79                                              0.78     507        H   NH.sub.2                NH.sub.2                    (6)                      COOC.sub.6 H.sub.4 (4')OCH.sub.3                                     0.78  0.80                                              0.79     508        H   NH.sub.2                NH.sub.2                    (6)                      COOC.sub.6 H.sub.4 (4')Cl                                     0.77  0.79                                              0.78     509        H   NH.sub.2                NH.sub.2                    (6)                      OC.sub.4 H.sub.9     0.73     510        H   NH.sub.2                NH.sub.2                    (6)                      O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                        0.75                                           0.75                                              0.74     511        H   NH.sub.2                NH.sub.2                    (6)                      OC.sub.6 H.sub.5                                     0.75                                        0.78                                           0.78                                              0.77     512        H   NH.sub.2                NH.sub.2                    (6)                      OC.sub.6 H.sub.4 (2')OC.sub.2 H.sub.5                                        0.78  0.77     513        H   NH.sub.2                NH.sub.2                    (6)                      OC.sub.6 H.sub.4 (3')CH.sub.3                                     0.76     0.77     514        H   NH.sub.2                NH.sub.2                    (6)                      OC.sub.6 H.sub.4 (3')F                                     0.76  0.78     515        H   NH.sub.2                NH.sub.2                    (6)                      OC.sub.6 H.sub.4 (4')CH.sub.3                                     0.76  0.78                                              0.77     516        H   NH.sub.2                NH.sub.2                    (6)                      OC.sub.6 H.sub.4 (4')OCH.sub.3                                        0.79  0.78     517        H   NH.sub.2                NH.sub.2                    (6)                      OC.sub.6 H.sub.4 (4')SCH.sub.3                                        0.78     518        H   NH.sub.2                NH.sub.2                    (6)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.75                                        0.78  0.76     519        H   NH.sub.2                NH.sub.2                    (6)                      CN                0.72     520        H   NH.sub.2                NH.sub.2                    (6)                      Br                0.72     521        H   NH.sub.2                NH.sub.2                    (7)                      CH.sub.3          0.71  0.70     522        H   NH.sub.2                NH.sub.2                    (7)                      2-Oxazolinyl   0.75  0.77                                              0.76     523        H   NH.sub.2                NH.sub.2                    (7)                      CONHC.sub.6 H.sub.5                                     0.75  0.77                                              0.76     524        H   NH.sub.2                NH.sub.2                    (7)                      COOC.sub.5 H.sub.11                                     0.71  0.74                                              0.73     525        H   NH.sub.2                NH.sub.2                    (7)                      COOC.sub.6 H.sub.5                                        0.79  0.78     526        H   NH.sub.2                NH.sub.2                    (7)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                     0.77  0.79                                              0.79     527        H   NH.sub.2                NH.sub.2                    (7)                      COOC.sub.6 H.sub.4 (4')CH.sub.3                                     0.78  0.80     528        H   NH.sub.2                NH.sub.2                    (7)                      OCH.sub.2 C.sub.6 H.sub.5                                        0.73     529        H   NH.sub.2                NH.sub.2                    (7)                      OC.sub.6 H.sub.5                                     0.75                                        0.78                                           0.78                                              0.77     530        H   NH.sub.2                NH.sub.2                    (7)                      OC.sub.6 H.sub.4 (2')Cl                                     0.76  0.78                                              0.77     531        H   NH.sub.2                NH.sub.2                    (7)                      OC.sub.6 H.sub.4 (3')F                                     0.76  0.78                                              0.77     532        H   NH.sub.2                NH.sub.2                    (7)                      OC.sub.6 H.sub.4 (4')CH.sub.3                                        0.78  0.77     533        H   NH.sub.2                NH.sub.2                    (7)                      OC.sub.6 H.sub.4 (4')OCH.sub.3                                     0.76                                        0.79  0.78     534        H   NH.sub.2                NH.sub.2                    (7)                      OC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.77  0.79     535        H   NH.sub.2                NH.sub.2                    (7)                      OC.sub.6 H.sub.4 (4')SCH.sub.3                                        0.78                                           0.78                                              0.77     536        H   NH.sub.2                NH.sub.2                    (7)                      OC.sub.6 H.sub.4 (4')COOC.sub.2 H.sub.5                                     0.76                                        0.78                                           0.78                                              0.77     537        H   NH.sub.2                NH.sub.2                    (7)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.78                                           0.77                                              0.76     538        H   NH.sub.2                NH.sub.2                    (7)                      OC.sub.6 H.sub.4 (4')Cl                                        0.78                                           0.77     539        H   NH.sub.2                NH.sub.2                    (7)                      O2-Naphthyl       0.79     540        H   NH.sub.2                NH.sub.2                    (7)                      CN                0.72                                           0.72     541        H   NH.sub.2                NH.sub.2                    (7)                      Cl                0.71                                           0.71     542        NH.sub.2            H   NH.sub.2                    (2)                      CH.sub.3             0.71                                              0.70     543        NH.sub.2            H   NH.sub.2                    (2)                      2-Oxazolinyl      0.77  0.76     544        NH.sub.2            H   NH.sub.2                    (2)                      CONHC.sub.6 H.sub.5                                        0.78                                           0.77                                              0.76     545        NH.sub.2            H   NH.sub.2                    (2)                      COOC.sub.5 H.sub.11                                        0.74                                           0.74                                              0.73     546        NH.sub.2            H   NH.sub.2                    (2)                      COOC.sub.6 H.sub.5                                        0.79  0.78     547        NH.sub.2            H   NH.sub.2                    (2)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.79     548        NH.sub.2            H   NH.sub.2                    (2)                      OCH.sub.3            0.71                                              0.70     549        NH.sub.2            H   NH.sub.2                    (2)                      OC.sub.6 H.sub.5  0.78                                           0.78                                              0.77     550        NH.sub.2            H   NH.sub.2                    (2)                      OC.sub.6 H.sub.4 (4')Cl                                        0.78                                           0.77     551        NH.sub.2            H   NH.sub.2                    (3)                      CH.sub.3       0.68     0.70     552        NH.sub.2            H   NH.sub.2                    (3)                      2-Oxazolinyl   0.75  0.77     553        NH.sub.2            H   NH.sub.2                    (3)                      COOCH.sub.3       0.75     554        NH.sub.2            H   NH.sub.2                    (3)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                        0.80                                           0.79     555        NH.sub.2            H   NH.sub.2                    (3)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                        0.81                                           0.81                                              0.80     556        NH.sub.2            H   NH.sub.2                    (3)                      OCH.sub.3         0.71                                           0.71     557        NH.sub.2            H   NH.sub.2                    (3)                      OCH.sub.2 C.sub.6 H.sub.5                                        0.73                                           0.73                                              0.72     558        NH.sub.2            H   NH.sub.2                    (3)                      OC.sub.6 H.sub.5                                     0.75                                        0.78                                           0.78                                              0.77     559        NH.sub.2            H   NH.sub.2                    (3)                      OC.sub.6 H.sub.4 (2')OC.sub.2 H.sub.5                                     0.76                                        0.78  0.77     560        NH.sub.2            H   NH.sub.2                    (3)                      OC.sub.6 H.sub.4 (3')F                                     0.76                                        0.78                                           0.78                                              0.77     561        NH.sub.2            H   NH.sub.2                    (3)                      OC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.77                                        0.79                                           0.79                                              0.78     562        NH.sub.2            H   NH.sub.2                    (3)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.75                                        0.78                                           0.77                                              0.76     563        NH.sub.2            H   NH.sub.2                    (3)                      CN                   0.72     564        NH.sub.2            H   NH.sub.2                    (7)                      CH.sub.3          0.71                                           0.71     565        NH.sub.2            H   NH.sub.2                    (7)                      2-Oxazolinyl      0.77                                           0.77     566        NH.sub.2            H   NH.sub.2                    (7)                      CONHC.sub.6 H.sub.5                                        0.78                                           0.77     567        NH.sub.2            H   NH.sub.2                    (7)                      COOC.sub.5 H.sub.11                                        0.74                                           0.74     568        NH.sub.2            H   NH.sub.2                    (7)                      COOC.sub.6 H.sub.5                                        0.79                                           0.79     569        NH.sub.2            H   NH.sub.2                    (7)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                     0.77                                        0.80                                           0.79                                              0.79     570        NH.sub.2            H   NH.sub.2                    (7)                      CN                0.72     571        NH.sub.2            H   NH.sub.2                    (7)                      Cl                0.71     572        NH.sub.2            H   H   (3)                      CH.sub.3       0.67  0.70     573        NH.sub.2            H   H   (3)                      CH.sub.2 CH(CH.sub.3).sub.2                                     0.74                                        0.76  0.75     574        NH.sub.2            H   H   (3)                      2-Oxazolinyl   0.74                                        0.76                                           0.76     575        NH.sub.2            H   H   (3)                      CONHC.sub.6 H.sub.5                                     0.74  0.76                                              0.75     576        NH.sub.2            H   H   (3)                      COOCH.sub.3          0.74                                              0.73     577        NH.sub.2            H   H   (3)                      COOC.sub.3 H.sub.7                                     0.69  0.71     578        NH.sub.2            H   H   (3)                      COOC.sub. 5 H.sub.11                                     0.70                                        0.73  0.72     579        NH.sub.2            H   H   (3)                      COOC.sub.6 H.sub.5                                     0.76                                        0.79  0.77     580        NH.sub.2            H   H   (3)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                        0.79                                           0.79                                              0.78     581        NH.sub.2            H   H   (3)                      COOC.sub.6 H.sub.4 (4')CH.sub.3                                     0.77                                        0.79                                           0.79     582        NH.sub.2            H   H   (3)                      COOC.sub.6 H.sub.4 (4')OCH.sub.3                                     0.77                                        0.79                                           0.79     583        NH.sub.2            H   H   (3)                      COOC.sub.6 H.sub.4 (4')Cl                                     0.76                                        0.78                                           0.78     584        NH.sub.2            H   H   (3)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.78                                           0.78     585        NH.sub.2            H   H   (3)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                        0.80                                           0.80                                              0.79     586        NH.sub.2            H   H   (3)                      OCH.sub.3         0.70     587        NH.sub.2            H   H   (3)                      OC.sub.4 H.sub.9  0.72                                           0.72                                              0.71     588        NH.sub.2            H   H   (3)                      OCH.sub.2 C.sub.6 H.sub.5                                        0.72                                           0.72                                              0.71     589        NH.sub.2            H   H   (3)                      O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                        0.74                                           0.74                                              0.72     590        NH.sub.2            H   H   (3)                      OC.sub.6 H.sub.5                                     0.74                                        0.77                                           0.77                                              0.76     591        NH.sub.2            H   H   (3)                      OC.sub.6 H.sub.4 (2')OC.sub.2 H.sub.5                                        0.77  0.76     592        NH.sub.2            H   H   (3)                      OC.sub.6 H.sub.4 (2')Cl                                     0.75  0.77                                              0.76     593        NH.sub.2            H   H   (3)                      OC.sub.6 H.sub.4 (3')CH.sub.3                                     0.75                                        0.77                                           0.77                                              0.76     594        NH.sub.2            H   H   (3)                      OC.sub.6 H.sub.4 (3')Cl                                     0.76                                        0.78                                           0.78                                              0.77     595        NH.sub.2            H   H   (3)                      OC.sub.6 H.sub.4 (3')F                                     0.75                                        0.77                                           0.77                                              0.76     596        NH.sub.2            H   H   (3)                      OC.sub.6 H.sub.4 (4')CH.sub.3                                     0.75                                        0.77                                           0.76     597        NH.sub.2            H   H   (3)                      OC.sub.6 H.sub.4 (4')OCH.sub.3                                     0.75  0.78                                              0.77     598        NH.sub.2            H   H   (3)                      OC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                        0.79                                           0.78                                              0.77     599        NH.sub.2            H   H   (3)                      OC.sub.6 H.sub.4 (4')SCH.sub.3                                        0.77     600        NH.sub.2            H   H   (3)                      OC.sub.6 H.sub.4 (4')COOC.sub.2 H.sub.5                                           0.77                                              0.76     601        NH.sub.2            H   H   (3)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.74                                        0.77                                           0.76                                              0.75     602        NH.sub.2            H   H   (3)                      OC.sub.6 H.sub.4 (4')Cl                                     0.74                                        0.77                                           0.76     603        NH.sub.2            H   H   (3)                      O 2-Naphthyl      0.78  0.77     604        NH.sub.2            H   H   (3)                      CN             0.68                                        0.71                                           0.71     605        NH.sub.2            H   H   (3)                      CF.sub.3          0.73                                           0.74     606        NH.sub.2            H   H   (2)                      CH.sub.3          0.70     607        NH.sub.2            H   H   (2)                      2-Oxazolinyl   0.74                                        0.76                                           0.76     608        NH.sub.2            H   H   (2)                      CONHC.sub.6 H.sub.5                                     0.74                                        0.77                                           0.76     609        NH.sub.2            H   H   (2)                      COOC.sub.6 H.sub.5                                     0.76                                        0.79  0.77     610        NH.sub.2            H   H   (2)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                           0.79     611        NH.sub.2            H   H   (2)                      COOC.sub.6 H.sub.4 (4')CH.sub.3                                        0.79                                           0.79                                              0.78     612        NH.sub.2            H   H   (2)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.78                                        0.80     613        NH.sub.2            H   H   (2)                      O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                        0.74                                           0.74                                              0.72     614        NH.sub.2            H   H   (2)                      OC.sub.6 H.sub.5  0.77                                           0.77                                              0.76     615        NH.sub.2            H   H   (2)                      OC.sub.6 H.sub.4 (3')CH.sub.3                                        0.77                                           0.77                                              0.76     616        NH.sub.2            H   H   (2)                      OC.sub.6 H.sub.4 (3')F                                     0.75  0.77     617        NH.sub.2            H   H   (2)                      OC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                        0.79  0.77     618        NH.sub.2            H   H   (2)                      OC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                     0.74                                        0.77                                           0.76                                              0.75     619        NH.sub.2            H   H   (2)                      CN                0.71     620        H   H   NH.sub.2                    (7)                      CH.sub.3          0.63     621        H   H   NH.sub.2                    (7)                      CH.sub.2 CH(CH.sub.3).sub.2                                        0.70     622        H   H   NH.sub.2                    (7)                      2-Oxazolinyl         0.69     623        H   H   NH.sub.2                    (7)                      COOC.sub.3 H.sub.7                                     0.61  0.64     624        H   H   NH.sub.2                    (7)                      COOC.sub.5 H.sub.11  0.66     625        H   H   NH.sub.2                    (7)                      COOC.sub.6 H.sub.5                                     0.70                                        0.73                                           0.72     626        H   H   NH.sub.2                    (7)                      COOC.sub.6 H.sub.4 (4')CH.sub.3                                     0.71                                        0.73                                           0.72     627        H   H   NH.sub.2                    (7)                      OC.sub.4 H.sub.9  0.65     628        H   H   NH.sub.2                    (7)                      CN                0.64     629        H   H   NH.sub.2                    (2)                      CH.sub.2 CH(CH.sub.3).sub.2                                     0.67                                        0.70     630        H   H   NH.sub.2                    (2)                      2-Oxazolinyl   0.67                                        0.70     631        H   H   NH.sub.2                    (2)                      CONHC.sub.6 H.sub.5                                        0.70     632        H   H   NH.sub.2                    (2)                      COOC.sub.6 H.sub.5                                     0.70                                        0.73                                           0.72                                              0.71     633        H   H   NH.sub.2                    (2)                      COOC.sub.6 H.sub.4 (3')CH.sub.3                                     0.70                                        0.73                                           0.73                                              0.71     634        H   H   NH.sub.2                    (2)                      COOC.sub.6 H.sub.4 (4')COOC.sub.5 H.sub.11                                        0.72                                           0.72                                              0.71     635        H   H   NH.sub.2                    (2)                      CN                0.64     636        H   NH.sub.2                H   (6)                      CH.sub.3       0.67                                        0.70     637        H   NH.sub.2                H   (6)                      CH.sub.2 CH(CH.sub.3).sub.2                                        0.76                                           0.76     638        H   NH.sub.2                H   (6)                      2-Oxazolinyl      0.76                                           0.76     639        H   NH.sub.2                H   (6)                      COOC.sub.6 H.sub.5                                     0.76                                        0.79                                           0.78                                              0.77     640        H   NH.sub.2                H   (6)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.78  0.80                                              0.79     641        H   NH.sub.2                H   (6)                      CN                0.71                                           0.71     642        H   NH.sub.2                H   (6)                      Cl                0.70                                           0.70     643        H   NH.sub.2                H   (2)                      CH.sub.3          0.70                                           0.70     644        H   NH.sub.2                H   (2)                      CH.sub.2 CH(CH.sub.3).sub.2                                        0.76     645        H   NH.sub.2                H   (2)                      COOC.sub.5 H.sub.11                                        0.73                                           0.73     646        H   NH.sub.2                H   (2)                      COOC.sub.6 H.sub.5                                     0.76                                        0.79                                           0.78                                              0.77     647        H   NH.sub.2                H   (2)                      COOC.sub.6 H.sub.4 (4')OCH.sub.3                                        0.79                                           0.79     648        H   NH.sub.2                H   (2)                      COOC.sub.6 H.sub.4 (4')C.sub.6 H.sub.5                                     0.78                                        0.80     649        H   NH.sub.2                H   (2)                      OCH.sub.3         0.70     650        H   NH.sub.2                H   (2)                      CN                0.71     651        NH.sub.2            H   H   (3)                      CONHCH.sub.3   0.69                                        0.75                                           0.76                                              0.73     652        NH.sub.2            H   H   (3)                      CONHC.sub.4 H.sub.9                                     0.70                                        0.76                                           0.77                                              0.74     653        NH.sub.2            H   H   (3)                      CONHC.sub.5 H.sub.11                                     0.71                                        0.76                                           0.77                                              0.75     654        NH.sub.2            H   H   (3)                      COSC.sub.6 H.sub.5                                     0.74     655        NH.sub.2            H   H   (3)                      COSC.sub.6 H.sub.4 (4')CH.sub.3                                           0.76     656        NH.sub.2            H   H   (3)                      COSC.sub.6 H.sub.4 (4')Cl                                        0.77     657        NH.sub.2            H   H   (3)                      COSC.sub.6 H.sub.4 (4')C(CH.sub.3).sub.3                                              0.75     658        SAr H   H   (2)                      CONHC.sub.5 H.sub.11                                     0.73                                        0.78                                           0.77                                              0.76     659        SAr H   H   (2)                      COSC.sub.6 H.sub.4 (4')CH.sub.3                                           0.77     660        SAr H   H   (2)                      CH.sub.2 C.sub.6 H.sub.5                                     0.74                                        0.75                                           0.76                                              0.73     661        NH.sub.2            H   H   (3)                      CH.sub.2 C.sub. 6 H.sub.5                                     0.73                                        0.73     662        NH.sub.2            H   H   (3)                      CH.sub.2 C.sub.6 H.sub.4 (4')CH.sub.3                                        0.74                                           0.75     663        NH.sub.3            H   H   (3)                       ##STR9##      0.73  0.75                                              0.74     664        NH.sub.3            H   H   (3)                       ##STR10##     0.72  0.75                                              0.73     665        SAR H   H   (2)                       ##STR11##     0.73                                        0.77  0.75     666        NH.sub.3            SAr SAr (3)                       ##STR12##     0.74                                        0.80  0.77     __________________________________________________________________________

Table 3 below relates to dyestuffs of the formula ##STR13## X₁ indicates the position of the substituent Q₁ and X₂ indicates the position of the substituent Q₂.

In other respects the information given for Table 2 applies.

                                      TABLE 3     __________________________________________________________________________     Y'    Y" Y"'                 X.sub.1                    Q.sub.1 X.sub.2                               Q.sub.2 S.sub.1                                          S.sub.2                                             S.sub.3                                                S.sub.4     __________________________________________________________________________     667        H  SAr              H  (2)                    COOC.sub.6 H.sub.5                            (6)                               COOC.sub.6 H.sub.5                                       0.78                                          0.80                                             0.81                                                0.79     668        H  SAr              H  (2)                    COOC.sub.5 H.sub.11                            (6)                               COOC.sub.5 H.sub.11                                       0.76                                          0.81                                             0.80                                                0.78     669        H  H  SAr                 (2)                    COOC.sub.6 H.sub.4 (3')F                            (7)                               COOC.sub.6 H.sub.3')F                                       0.69                                          0.75                                             0.74                                                0.73     670        H  H  SAr                 (2)                    COOC.sub.5 H.sub.11                            (7)                               COOC.sub.5 H.sub.11                                       0.67                                          0.73                                             0.72                                                0.70     671        NH.sub.2           SAr              NH.sub.2                 (3)                    COOC.sub.6 H.sub.5                            (7)                               COOC.sub.6 H.sub.5                                       0.78                                          0.80                                             0.81                                                0.79     672        NH.sub.2           SAr              NH.sub.2                 (3)                    COOC.sub.5 H.sub.11                            (7)                               COOC.sub.5 H.sub.11                                       0.75  0.79     673        NH.sub.2           NH.sub.2              SAr                 (3)                    COOC.sub.6 H.sub.5                            (6)                               COOC.sub.6 H.sub.5                                       0.77                                          0.79  0.76     674        NH.sub.2           NH.sub.2              SAr                 (3)                    COOC.sub.5 H.sub.11                            (6)                               COOC.sub.5 H.sub.11                                       0.75                                          0.77                                             0.78     __________________________________________________________________________ 

We claim:
 1. Anthraquinone dyestuffs of the formula ##STR14## in which R₁ represents --CO--X--alkyl, --CO--X--aralkyl, --CO--X--aryl, --O--aryl, --CF₃ or a heterocyclic radical, said heterocyclic radical being an unsubstituted or substituted, fused or unfused ring carrying a 5-ring or a 6-ring heterocyclic structure of the oxazole, oxdiazole, thiazole, thiadiazole, imidazole, triazole, oxazoline or dihydro-H-oxazine series, andR₂ represents H, alkyl, aralkyl, --CO--X--alkyl, --CO--X--aralkyl, --CO--X--aryl, --O--alkyl, --O--aralkyl, --O--aryl, --CN, --NO₂, --CF₃, halogen or a heterocyclic radical, said heterocyclic radical being an unsubstituted or substituted, fused or unfused ring carrying a 5-ring or a 6-ring heterocyclic structure of the oxazole, oxdiazole, thiazole, thiadiazole, imidazole, triazole, oxazoline or dihydro-H-oxazine series, and X represents O, S, NH or a direct bond and Y₁, Y₂, Y₃ and Y₄ denotes hydrogen, NH₂, OH, halogen, or NO₂ or an arylmercapto group and at least one of the substituents Y₁, Y₂, Y₃, or Y₄ representing an arylmercapto group,the alkyl, aryl, aralkyl and heterocyclic radicals mentioned for R₁ and Y₁, Y₂, Y₃ and Y₄ being substituted or unsubstituted and the alkyl chains being non-interrupted or interrupted by 1, 2 or 3 non-adjacent oxygen atoms.
 2. Anthraquinone dyestuffs of the formula ##STR15## in which R₆ represents alkyl, aralkyl, --CO--X--alkyl, --CO--X--aralkyl, --CO--X--aryl, --O--aryl, --CF₃, or a heterocyclic radical, said heterocyclic radical being an unsubstituted or substituted, fused or unfused ring carrying a 5-ring or a 6-ring heterocyclic structure of the oxazole, oxdiazole, thiazole, thiadiazole, imidazole, triazole, oxazoline or dihydro-H-oxazine series, andR₇ represents H, alkyl, aralkyl, --CO--X--alkyl, --CO--X--aralkyl, --CO--X--aryl, --O--aryl, --CN, --NO₂ --CF₃, halogen or a heterocyclic radical, said heterocyclic radical being an unsubstituted or substituted, fused or unfused ring carrying a 5-ring or a 6-ring heterocyclic structure of the oxazole, oxdiazole, thiazole, thiadiazole, imidazole, triazole, oxazoline or dihydro-H-oxazine series, and X representing O, S, NH or a direct bond and Y₁, Y₂, Y₃ and Y₄ represent the following combinations:

    ______________________________________     Y.sub.1     Y.sub.2    Y.sub.3    Y.sub.4     ______________________________________     S--Ar       S--Ar      S--Ar      NH.sub.2     S--Ar       S--Ar      NH.sub.2   S--Ar     S--Ar       NH.sub.2   S--Ar      S--Ar     NH.sub.2    S--Ar      S--Ar      S--Ar     S--Ar       S--Ar      S--Ar      H     S--Ar       S--Ar      H          S--Ar     S--Ar       H          S--Ar      S--Ar     H           S--Ar      S--Ar      S--Ar     S--Ar       S--Ar      NH.sub.2   NH.sub.2     NH.sub.2    NH.sub.2   S--Ar      S--Ar     S--Ar       NH.sub.2   NH.sub.2   S--Ar     NH.sub.2    S--Ar      S--Ar      NH.sub.2     S--Ar       NH.sub.2   S--Ar      NH.sub.2     NH.sub.2    S--Ar      NH.sub.2   S--Ar     S--Ar       S--Ar      NH.sub.2   OH     S--Ar       S--Ar      OH         NH.sub.2     NH.sub.2    OH         S--Ar      S--Ar     OH          NH.sub.2   S--Ar      S--Ar     S--Ar       NH.sub.2   S--Ar      OH     NH.sub.2    S--Ar      OH         S--Ar     S--Ar       OH         S--Ar      NH.sub.2     OH          S--Ar      NH.sub.2   S--Ar     S--Ar       S--Ar      NH.sub.2   Hal     S--Ar       S--Ar      Hal        NH.sub.2     NH.sub.2    Hal        S--Ar      S--Ar     Hal         NH.sub.2   S--Ar      S--Ar     S--Ar       NH.sub.2   S--Ar      Hal     NH.sub.2    S--Ar      Hal        S--Ar     S--Ar       Hal        S--Ar      NH.sub.2     Hal         S--Ar      NH.sub.2   S--Ar     S--Ar       S--Ar      NH.sub.2   H     S--Ar       S--Ar      H          NH.sub.2     NH.sub.2    H          S--Ar      S--Ar     H           NH.sub.2   S--Ar      S--Ar     S--Ar       NH.sub.2   S--Ar      H     NH.sub.2    S--Ar      H          S--Ar     S--Ar       H          S--Ar      NH.sub.2     H           S--Ar      NH.sub.2   S--Ar     S--Ar       OH         S--Ar      Hal     OH          S--Ar      Hal        S--Ar     S--Ar       Hal        S--Ar      OH     Hal         S--Ar      OH         S--Ar     S--Ar       S--Ar      OH         H     S--Ar       S--Ar      H          OH     OH          H          S--Ar      S--Ar     H           OH         S--Ar      S--Ar     S--Ar       OH         S--Ar      H     OH          S--Ar      H          S--Ar     S--Ar       H          S--Ar      OH     H           S--Ar      OH         S--Ar     S--Ar       Hal        S--Ar      H     Hal         S--Ar      H          S--Ar     S--Ar       H          S--Ar      Hal     H           S--Ar      Hal        S--Ar     S--Ar       S--Ar      H          H     H           H          S-- Ar     S--Ar     S--Ar       H          S--Ar      H     H           S--Ar      H          S--Ar     S--Ar       NH.sub.2   NH.sub.2   NH.sub.2     NH.sub.2    S--Ar      NH.sub.2   NH.sub.2     NH.sub.2    NH.sub.2   S--Ar      NH.sub.2     NH.sub.2    NH.sub.2   NH.sub.2   S--Ar     S--Ar       NH.sub.2   NH.sub.2   OH     NH.sub.2    S--Ar      OH         NH.sub.2     NH.sub.2    OH         S--Ar      NH.sub.2     OH          NH.sub.2   NH.sub.2   S--Ar     S--Ar       OH         NH.sub.2   NH.sub.2     OH          S--Ar      NH.sub.2   NH.sub.2     NH.sub.2    NH.sub.2   S--Ar      OH     NH.sub.2    NH.sub.2   OH         S--Ar     S--Ar       NH.sub.2   OH         NH.sub.2     NH.sub.2    S--Ar      NH.sub.2   OH     OH          NH.sub.2   S--Ar      NH.sub.2     NH.sub.2    OH         NH.sub.2   S--Ar     S--Ar       NH.sub.2   NO.sub.2   NH.sub.2     NH.sub.2    S--Ar      NH.sub.2   NO.sub.2     NO.sub.2    NH.sub.2   S--Ar      NH.sub.2     NH.sub.2    NO.sub.2   NH.sub.2   S--Ar     S--Ar       NH.sub.2   NH.sub.2   H     NH.sub.2    S--Ar      H          NH.sub.2     NH.sub.2    H          S--Ar      NH.sub.2     H           NH.sub.2   NH.sub.2   S--Ar     S--Ar       H          NH.sub.2   NH.sub.2     H           S-- Ar     NH.sub.2   NH.sub.2     NH.sub.2    NH.sub.2   S--Ar      H     NH.sub.2    NH.sub.2   H          S--Ar     S--Ar       NH.sub.2   H          NH.sub.2     NH.sub.2    S--Ar      NH.sub.2   H     H           NH.sub.2   S--Ar      NH.sub.2     NH.sub.2    H          NH.sub.2   S--Ar     S--Ar       NH.sub.2   H          H     NH.sub.2    S--Ar      H          H     H           H          S--Ar      NH.sub.2     H           H          NH.sub.2   S--Ar     S--Ar       H          NH.sub.2   H     H           S--Ar      H          NH.sub.2     NH.sub.2    H          S--Ar      H     H           NH.sub.2   H          S--Ar     ______________________________________

wherein Ar denotes aryl and Hal denotes halogen.
 3. Anthraquinone dyestuffs of the formulas ##STR16## in which R₃ is ##STR17## --OR₄ or --SR₄, R₃ is ##STR18## Y₂, Y₃ and Y₄ ' denote unsubstituted or substituted arylmercapto,Y₅ denotes --NH₂, --OH or unsubstituted or substituted arylmercapto, R₄ and R₅ denote unsubstituted or substituted alkyl which is uninterrupted or interrupted in the C chain by one or more O and/or S atoms, or denotes unsubstitued or substituted aryl, R₄ ' denotes unsubstituted or substituted aryl and X₁ denotes O, S or --NH.
 4. Anthraquinone dyestuffs of the formulas ##STR19## in which R₃, R₃ ', Y₂ ', Y₃ ', Y₄ ' and Y₅ have the meanings indicated in claim 1 andY₃ ' denotes unsubstituted or substituted arylmercapto.
 5. Anthraquinone dyestuffs of the formula ##STR20## in which R₃, Y₂ ', Y₃ ', Y₄ ' and Y₅ have the meanings indicated in claims 3 and
 4. 6. Anthraquinone dyestuffs of the formulas ##STR21## in which R₄, Y₃ ' and Y₄ ' have the meanings indicated in claims 3 and
 4. 7. Anthraquinone dyestuffs of the formulas ##STR22## in which R₃ " denotes --OR₄ or --SR₄,R₄ and R₅ denote unsubstituted or substituted alkyl or unsubstituted or substituted aryl and Y₆ and Y₇ denote --NH₂, --OH or --SR₄, one of the two radicals Y₆ and Y₇ being --SR₄.
 8. In a method of dyeing synthetic polymers, wherein the improvement comprises conducting said dyeing with dyestuffs according to claim
 1. 9. Dichroic material containing about 0.01 to about 30% by weight of at least one dyestuff according to claim
 3. 10. Dichroic material containing about 0.01 to about 30% by weight of at least one dyestuff according to claim
 4. 11. Dichroic material containing about 0.01 to about 30% by weight of at least one dyestuff according to claim
 5. 12. Dichroic material containing about 0.01 to about 30% by weight of at least one dyestuff according to claim
 6. 13. Dichroic material containing about 0.01 to about 30% by weight of at least one dyestuff according to claim
 7. 14. Dichroic material containing about 0.01 to about 30% by weight of at least one dyestuff of the formula ##STR23## in which R₈ represents --CO--X--alkyl, --CO--X--aralkyl, --CO--X--aryl, --O--alkyl, --O--aralkyl, --O--aryl, --CF₃, or a heterocyclic radical, said heterocyclic radical being an unsubstituted or substituted, fused or unfused ring carrying a 5-ring or a 6-ring heterocyclic structure of the oxazole, oxdiazole, thiazole, thiadiazole, imidazole, triazole, oxazoline, or dihydro-H-oxazine series, andR₉ represents H or R₈, X represents O, S, NH or a direct bond and Y₁, Y₂, Y₃ and Y₄ represent the following combinations:

    ______________________________________     Y.sub.1     Y.sub.2    Y.sub.3    Y.sub.4     ______________________________________     S--Ar       S--Ar      S--Ar      NH.sub.2     S--Ar       S--Ar      NH.sub.2   S--Ar     S--Ar       NH.sub.2   S--Ar      S--Ar     NH.sub.2    S--Ar      S--Ar      S--Ar     S--Ar       S--Ar      S--Ar      H     S--Ar       S--Ar      H          S--Ar     S--Ar       H          S--Ar      S--Ar     H           S--Ar      S--Ar      S--Ar     S--Ar       S--Ar      NH.sub.2   NH.sub.2     NH.sub.2    NH.sub.2   S--Ar      S--Ar     S--Ar       NH.sub.2   NH.sub.2   S--Ar     NH.sub.2    S--Ar      S--Ar      NH.sub.2     S--Ar       NH.sub.2   S--Ar      NH.sub.2     NH.sub.2    S--Ar      NH.sub.2   S--Ar     S--Ar       S--Ar      NH.sub.2   OH     S--Ar       S--Ar      OH         NH.sub.2     NH.sub.2    OH         S--Ar      S--Ar     OH          NH.sub.2   S--Ar      S--Ar     S--Ar       NH.sub.2   S--Ar      OH     NH.sub.2    S--Ar      OH         S--Ar     S--Ar       OH         S--Ar      NH.sub.2     OH          S--Ar      NH.sub.2   S--Ar     S--Ar       S--Ar      NH.sub.2   Hal     S--Ar       S--Ar      Hal        NH.sub.2     NH.sub.2    Hal        S--Ar      S--Ar     Hal         NH.sub.2   S--Ar      S--Ar     S--Ar       NH.sub.2   S--Ar      Hal     NH.sub.2    S--Ar      Hal        S--Ar     S--Ar       Hal        S--Ar      NH.sub.2     Hal         S--Ar      NH.sub.2   S--Ar     S--Ar       S--Ar      NH.sub.2   H     S--Ar       S--Ar      H          NH.sub.2     NH.sub.2    H          S--Ar      S--Ar     H           NH.sub.2   S--Ar      S--Ar     S--Ar       NH.sub.2   S--Ar      H     NH.sub.2    S--Ar      H          S--Ar     S--Ar       H          S--Ar      NH.sub.2     H           S--Ar      NH.sub.2   S--Ar     S--Ar       OH         S--Ar      Hal     OH          S--Ar      Hal        S--Ar     S--Ar       Hal        S--Ar      OH     Hal         S--Ar      OH         S--Ar     S--Ar       S--Ar      OH         H     S--Ar       S--Ar      H          OH     OH          H          S--Ar      S--Ar     H           OH         S--Ar      S--Ar     S--Ar       OH         S--Ar      H     OH          S--Ar      H          S--Ar     S--Ar       H          S--Ar      OH     H           S--Ar      OH         S--Ar     S--Ar       Hal        S--Ar      H     Hal         S--Ar      H          S--Ar     S--Ar       H          S--Ar      Hal     H           S--Ar      Hal        S--Ar     S--Ar       S--Ar      H          H     H           H          S-- Ar     S--Ar     S--Ar       H          S--Ar      H     H           S--Ar      H          S--Ar     S--Ar       NH.sub.2   NH.sub.2   NH.sub.2     NH.sub.2    S--Ar      NH.sub.2   NH.sub.2     NH.sub.2    NH.sub.2   S--Ar      NH.sub.2     NH.sub.2    NH.sub.2   NH.sub.2   S--Ar     S--Ar       NH.sub.2   NH.sub.2   OH     NH.sub.2    S--Ar      OH         NH.sub.2     NH.sub.2    OH         S--Ar      NH.sub.2     OH          NH.sub.2   NH.sub.2   S--Ar     S--Ar       OH         NH.sub.2   NH.sub.2     OH          S--Ar      NH.sub.2   NH.sub.2     NH.sub.2    NH.sub.2   S--Ar      OH     NH.sub.2    NH.sub.2   OH         S--Ar     S--Ar       NH.sub.2   OH         NH.sub.2     NH.sub.2    S--Ar      NH.sub.2   OH     OH          NH.sub.2   S--Ar      NH.sub.2     NH.sub.2    OH         NH.sub.2   S--Ar     S--Ar       NH.sub.2   NO.sub.2   NH.sub.2     NH.sub.2    S--Ar      NH.sub.2   NO.sub.2     NO.sub.2    NH.sub.2   S--Ar      NH.sub.2     NH.sub.2    NO.sub.2   NH.sub.2   S--Ar     S--Ar       NH.sub.2   NH.sub.2   H     NH.sub.2    S--Ar      H          NH.sub.2     NH.sub.2    H          S--Ar      NH.sub.2     H           NH.sub.2   NH.sub.2   S--Ar     S--Ar       H          NH.sub.2   NH.sub.2     H           S-- Ar     NH.sub.2   NH.sub.2     NH.sub.2    NH.sub.2   S--Ar      H     NH.sub.2    NH.sub.2   H          S--Ar     S--Ar       NH.sub.2   H          NH.sub.2     NH.sub.2    S--Ar      NH.sub.2   H     H           NH.sub.2   S--Ar      NH.sub.2     NH.sub.2    H          NH.sub.2   S--Ar     S--Ar       NH.sub.2   H          H     NH.sub.2    S--Ar      H          H     H           H          S--Ar      NH.sub.2     H           H          NH.sub.2   S--Ar     S--Ar       H          NH.sub.2   H     H           S--Ar      H          NH.sub.2     NH.sub.2    H          S--Ar      H     H           NH.sub.2   H          S--Ar     ______________________________________

wherein Ar denotes aryl and Hal denotes halogen.
 15. Dichroic material containing about 0.01 to about 30% by weight of at least one dyestuff according to claim 1, wherein R₁ has the given meaning.
 16. Dichroic material containing about 0.01 to about 30% by weight of at least one dyestuff according to claim 2, wherein R₆ has the given meaning. 